Dihalopropene compounds, insecticides containing them as active ingredients, and intermediates for their production

ABSTRACT

The present invention provides dihalopropene compounds of the general formula: wherein R1 is C1-C10 alkyl or the like; L is C(=O)NH or the like; R2, R3 and R4 are independently halogen or the like; R5, R6 and R7 are independently hydrogen or the like; m is an integer of 0 to 4; n is an integer of 0 to 2; X is chlorine or the like; Y is oxygen or the like; and Z is oxygen or the like, which have excellent insecticidal activity so that they are satisfactorily effective for the control of noxious insects.

This Application is a Divisional application of Ser. No. 08/913,879filed Sep. 24, 1997, now U.S. Pat. No. 5,952,386 which is the NationalPhase of PCT/JP96/00989 filed Apr. 11, 1996.

TECHNICAL FIELD

The present invention relates to dihalopropene compounds, insecticidescontaining them as active ingredients, and intermediates for theirproduction.

BACKGROUND ART

As disclosed in JP-A 48-86835/1973 and JP-A 49-1526/1974, for example,it is well known that some kinds of propene compounds can be used asactive ingredients of insecticides.

In view of their insecticidal activity, however, it cannot always besaid that these compounds are satisfactorily effective for the controlof noxious insects.

DISCLOSURE OF INVENTION

The present inventors have intensively studied to find a compound havingexcellent insecticidal activity. As a result, they have found thatparticular dihalopropene compounds have satisfactory insecticidalactivity for the control of noxious insects, thereby completing thepresent invention.

That is, the present invention provides dihalopropene compounds of thegeneral formula: ##STR2## wherein m is an integer of 0 to 4;

n is an integer of 0 to 2;

X's are independently chlorine or bromine;

Y is oxygen, NH or sulfur; and

Z is oxygen, sulfur or NR₁₅ in which R₁₅ is hydrogen or C₁ -C₃ alkyl;

R₂, R₃ and R₄ are independently halogen, C₁ -C₃ haloalkyl or C₁ -C₃alkyl;

R₅, R₆ and R₇ are independently hydrogen, C₁ -C₃ alkyl ortrifluoromethyl;

L is C═W, C(═W)NR₁₃, NR₁₃ C(═W), SO₂ NR₁₃, NR₁₃ SO₂, NR₁₃ C(═W₁)--W,WC(═W₁)NR₁₃ or NR₁₄ C(═W)NR₁₃ in which W and W₁ are independently oxygenor sulfur, and R₁₃ and R₁₄ are independently hydrogen, C₁ -C₁₀ alkyl, C₁-C₅ haloalkyl, C₂ -C₁₀ alkenyl, C₂ -C₆ haloalkenyl, C₃ -C₉ alkynyl or C₃-C₅ haloalkynyl;

R₁ is C₁ -C₁₀ alkyl, C₁ -C₅ haloalkyl, C₂ -C₁₀ alkenyl, C₂ -C₆haloalkenyl, C₃ -C₉ alkynyl, C₃ -C₅ haloalkynyl, C₂ -C₇ alkoxyalkyl, C₂-C₇ alkylthioalkyl,

C₃ -C₆ cycloalkyl optionally substituted with C₁ -C₄ alkyl, C₁ -C₄alkoxy or C₁ -C₃ haloalkoxy,

C₄ -C₉ cycloalkylalkyl optionally substituted with C₁ -C₄ alkyl,

C₅ -C₆ cycloalkenyl optionally substituted with C₁ -C₄ alkyl,

C₆ -C₈ cycloalkenylalkyl optionally substituted with C₁ -C₄ alkyl,

an optionally substituted heterocyclic group, Q₁, Q₂, Q₃ or Q₄ of thegeneral formula: ##STR3## in which M is oxygen, NH or sulfur,

l is an integer of 0 to 5,

is an integer of 0 to 5, and

q is an integer of 1 to 5;

R₁₂ is halogen, cyano, nitro, pentafluorosulfanyl (F₅ S), C₁ -C₈ alkyl,C₁ -C₃ haloalkyl, C₁ -C₇ alkoxy, C₁ -C₃ haloalkoxy, C₁ -C₃ alkylthio, C₁-C₃ haloalkylthio, C₃ -C₆ alkenyloxy, C₃ -C₆ haloalkenyloxy, C₁ -C₃hydroxyalkyl, C₂ -C₄ alkenyl, C₂ -C₄ haloalkenyl, C₂ -C₄ alkynyl, C₂ -C₄alkynyloxy, C₂ -C₄ haloalkynyl, C₂ -C₄ haloalkynyloxy, C₂ -C₄alkoxyalkyl, C₂ -C₄ alkylthioalkyl, C₃ -C₆ cycloalkyl, C₅ -C₆cycloalkenyl, C₂ -C₅ alkoxycarbonyl, C₃ -C₆ cycloalkyloxy, C₅ -C₆cycloalkenyloxy,

phenyl optionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy,

phenoxy optionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy,

benzyl optionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy,

benzyloxy optionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy;

or when l is an integer of 2 to 5, adjacent two R₁₂ are combinedtogether at their ends to form trimethylene or tetramethylene,methylenedioxy optionally substituted with halogen or C₁ -C₃ alkyl, orethylenedioxy optionally substituted with halogen or C₁ -C₃ alkyl; and

R₈, R₉, R₁₀ and R₁₁ are independently hydrogen, C₁ -C₃ alkyl ortrifluoromethyl.

The present invention further provides compounds of the general formula:##STR4## which are useful as intermediates for the production of some ofthe present compounds, wherein X's are independently chlorine orbromine; R₁₈ and R₁₉ are independently halogen or C₁ -C₃ alkyl; R₁₇ isamino or carboxyl; R₅, R₆ and R₇ are independently hydrogen, C₁ -C₃alkyl or trifluoromethyl; and m is an integer of 0 to 4. Moreparticularly, the present invention provides phenol compounds of thegeneral formula: ##STR5## wherein R₂₀ is Q₁ as defined above, or2-pyridyl, 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 2-thienyl,3-thienyl, 2-furyl, 3-furyl, 3-pyridyl or 4-pyridyl, each of which maybe optionally substituted with (R₁₆)s in which R₁₆ is halogen, nitro,cyano, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₃ haloalkoxy,C₁ -C₃ alkylthio, C₁ -C₃ haloalkylthio, C₁ -C₂ alkylsulfinyl, C₁ -C₂alkylsulfonyl, C₁ -C₂ haloalkylsulfinyl, C₁ -C₂ haloalkylsulfonyl, C₂-C₄ alkenyl, C₂ -C₄ haloalkenyl, C₂ -C₄ alkynyl, C₂ -C₄ haloalkynyl,amino, dimethylamino, acetamido, acetyl, haloacetyl, formyl, carboxyl,methoxycarbonyl, C₃ -C₆ cycloalkyl, (C₁ -C₂ alkyl)aminocarbonyl, [di(C₁-C₂ alkyl)amino]carbonyl,

phenyl optionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy,

benzyl optionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy,

phenoxy optionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy,

benzyloxy optionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy,

or pyridyloxy optionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy; and

s is an integer of 0 to 7;

R₂ and R₃ are independently halogen, C₁ -C₃ haloalkyl or C₁ -C₃ alkyl;

R₅, R₆ and R₇ are independently hydrogen, C₁ -C₃ alkyl ortrifluoromethyl;

L₁ is C═W, C(═W)NR₁₃₁ or SO₂ NR₁₃₁ in which W is oxygen or sulfur, andR₁₃₁ is hydrogen or C₁ -C₃ alkyl.

As more specific examples of these phenol compounds, the presentinvention provides phenol compounds wherein R₂₀ is Q₁ in which p=0 or R₁as defined above in which the 5- or 6-membered heterocyclic group is2-pyridyl, 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 2-thienyl,3-thienyl, 2-furyl, 3-furyl, 3-pyridyl or 4-pyridyl; and

phenol compounds wherein R₂₀ is Q₁ in which p=0 or R₁ as defined abovein which the 5- or 6-membered heterocyclic group is 2-pyridyl,2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl,2-furyl, 3-furyl, 3-pyridyl or 4-pyridyl, and L₁ is C(═W)NR₁₃₁ or SO₂NR₁₃₁ ; and

phenol compounds, wherein R₂₀ is Q₁ in which p=0 or R₁ as defined abovein which the 5- or 6-membered heterocyclic group is 2-pyridyl,2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl,2-furyl, 3-furyl, 3-pyridyl or 4-pyridyl; R₂ and R₃ are halogen or C₁-C₃ alkyl; and L₁ is C(═W)NR₁₃₁ or SO₂ NR₁₃₁ ;

and the following compounds:

3,5-dichloro-4-(3-(N-(4-trifluoromethylphenyl)carbamoyl)propyloxy)phenol;

3,5-dichloro-4-(4-(N-(4-trifluoromethylphenyl)carbamoyl)butyloxy)phenol;

3,5-dichloro-4-(3-(N-(5-trifluoromethyl-2-pyridyl)carbamoyl)propyloxy)phenol; and

3,5-dichloro-4-(4-(N-(5-trifluoromethyl-2-pyridyl)carbamoyl)butyloxy)phenol.

DETAILED DESCRIPTION OF THE INVENTION

The variables in the above formulas for the present compounds and theirintermediates can take the following specific examples.

Examples of the substituent on the optionally substituted heterocyclicgroup represented by R₁ are those of the formula: (R₁₆)_(s) in which R₁₆is halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ C₄ alkoxy,C₁ -C₃ haloalkoxy, C₁ -C₃ alkylthio, C₁ -C₃ haloalkylthio, C₁ -C₂alkylsulfinyl, C₁ -C₂ alkylsulfonyl, C₁ ₂ haloalkylsulfinyl, C₁ -C₂haloalkylsulfonyl, C₂ -C₄ alkenyl, C₂ -C₄ haloalkenyl, C₂ -C₄ alkynyl,C₂ -C₄ haloalkynyl, amino, dimethylamino, acetamido, acetyl, haloacetyl,formyl, carboxyl, methoxycarbonyl, C₃ -C₆ cycloalkyl, (C₁ -C₂alkyl)aminocarbonyl, [di(C₁ -C₂ alkyl)amino]carbonyl,

phenyl optionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy,

benzyl optionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy,

phenoxy optionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy,

benzyloxy optionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy,

or pyridyloxy optionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy; and

s is an integer of 0 to 7.

Examples of the halogen atom represented by R₂, R₃, R₄, R ₁₂, R₁₆, R₁₈or R₁₉, or present in R₁₂ or R₁₆, are fluorine, chlorine, bromine andiodine.

Examples of the C₁ -C₁₀ alkyl group represented by R₁, R₁₃ or R₁₄ aremethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl,tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl,n-heptyl, isohexyl, n-octyl, n-nonyl, n-decyl, 1-ethylpropyl,2-ethylbutyl, 1-methylpentyl, 1-ethylbutyl, 3-methylpentyl,1,3-dimethylbutyl, 1-methylheptyl and 1-methyloctyl.

Examples of the C₁ -C₃ alkyl group represented by R₂, R₃, R₄, R₅, R₆,R₇, R₈, R₉, R₁₀, R₁₁, R₁₅, R₁₈ or R₁₉ are methyl, ethyl, n-propyl andisopropyl.

Examples of the C₁ -C₈ alkyl group represented by R₁₂ are methyl, ethyl,n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl,isopentyl, neopentyl, tert-pentyl, 1-ethylpentyl, n-hexyl, isohexyl,2-ethylbutyl, 1-methylpentyl, 1-ethylbutyl, 3-methylpentyl,1,3-dimethylbutyl, n-heptyl, n-octyl and 1-methylheptyl.

Examples of the C₁ -C₂ alkyl group present in R₁₆ are methyl and ethyl.

Examples of the C₁ -C₅ haloalkyl group represented by R₁, R₁₃ or R₁₄ aretrifluoromethyl, difluoromethyl, bromodifluoromethyl,2,2,2-trifluoroethyl, perfluoroethyl, 2-fluoroethyl, 2-chloroethyl,2-bromoethyl, 2-iodoethyl, 2,2-dichloroethyl,2-bromo-1,1,2,2-tetrafluoroethyl, 1,1,2,2-tetrafluoroethyl,2-chloro-1,1,2-trifluoroethyl, 2-bromo-1,1,2-trifluoroethyl,2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 3-chloropropyl,3-bromopropyl, 3-fluoropropyl, 3-iodopropyl, 3,3,3-trifluoropropyl,2,2,3,3,3-pentafluoropropyl, 1,1,2,3,3,3-hexafluoropropyl,2-chloropropyl, 1-chloro-1-methylethyl, 1-bromo-1-methylethyl,2-fluoro-1-(fluoromethyl)ethyl, 2-chloro-1-(chloromethyl)ethyl,2-bromo-1-(bromomethyl)ethyl, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl,2,3-dibromopropyl, 4-fluorobutyl, 4-bromobutyl, 4-chlorobutyl,4-iodobutyl, 2-(bromomethyl)-propyl, 3-chloro-2,2-dimethyl-n-propyl,3-bromo-2,2-dimethylpropyl, 2,2,3,4,4,4-hexafluorobutyl,3-bromo-(1-bromomethyl)propyl and 2,2,3,3,4,4,5,5-octafluoropentyl.

Examples of the C₁ -C₃ haloalkyl group represented by R₂, R₃, R₄, R₁₂ orR₁₆, or present in R₁₂ or R₁₆, are trifluoromethyl, difluoromethyl,bromodifluoromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl,2-bromoethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl,2,2,3,3,3-pentafluoropropyl, 3,3,3-trifluoropropyl, 1-fluoropropyl,2-chloropropyl and 3-bromopropyl.

Examples of the C₂ -C₁₀ alkenyl group represented by R₁, R₁₃ or R₁₄ arevinyl, allyl, homoallyl, isopropenyl, 2-butenyl, 1-methyl-2-propenyl,prenyl, 3-methyl-3-butenyl, 1-ethyl-2-propenyl, 2-ethyl-2-propenyl,2-pentenyl, 2-methyl-2-butenyl, 1-methyl-2-butenyl, 2-methyl-3-butenyl,4-pentenyl, 1-methyl-3-butenyl, 1-ethyl-2-propenyl, 1-propyl-2-propenyl,3-hexenyl, 2-isopropyl-2-propenyl, 2-ethyl-2-butenyl,2-methyl-2-pentenyl, 1-ethyl-2-butenyl, 1-methyl-4-pentenyl,1,3-dimethyl-2-butenyl, 2-hexenyl, 4-hexenyl, 5-hexenyl,1-n-propyl-2-propenyl, 1-allyl-3-butenyl, 2-heptenyl,1,5-dimethyl-4-hexenyl, 1-pentyl-2-propenyl, 1,7-dimethyl-6-octenyl andgeranyl.

Examples of the C₂ -C₆ haloalkenyl group represented by R₁, R₁₃ or R₁₄are 2-chloroethenyl, 2,2-dichloroethenyl, 3-chloro-2-propenyl,3-bromo-2-propenyl, 2-chloro-2-propenyl, 2-bromo-2-propenyl,3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl,3,3-difluoro-2-propenyl, 2-chloromethyl-2-propenyl, 4-chloro-2-butenyl,4-chloro-2-butenyl, 3-chloro-4,4,4-trifluoro-2-butenyl,4-bromo-3-fluoro-4,4-difluoro-2-butenyl, 3,4,4,4-tetrafluoro-2-butenyl,4,4-dichloro-3-butenyl, 4,4-dibromo-3-butenyl,4,4,4-trifluoro-3-butenyl, 3-chloro-2-butenyl and6,6-dichloro-5-hexenyl.

Examples of the C₂ -C₄ alkenyl group represented by R₁₂ or R₁₆ arevinyl, isopropenyl, 1-propenyl, 2-ethyl-1-propenyl, 1-methyl-1-propenyl,allyl, 2-methylpropenyl and 2-butenyl.

Examples of the C₂ -C₄ haloalkenyl group represented by R₁₂ or R₁₆ are2,2-dichloroethenyl, 2,2-dibromoethenyl, 3,3-dichloroallyl,3,3-dibromoallyl, 2,3-dichloroallyl, 2,3-dibromoallyl,2-chloro-2-propenyl, 3-chloro-2-propenyl, 2-bromo-2-propenyl and3-chloro-2-butenyl.

Examples of the C₃ -C₉ alkynyl group represented by R₁, R₁₃ or R₁₄ are2-propynyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl,2-methyl-3-butynyl, 1-methyl-3-butynyl, 2-pentynyl, 4-pentynyl,3-pentynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 5-hexynyl,1-pentyl-2-propynyl and 3-nonynyl.

Examples of the C₃ -C₅ haloalkynyl group represented by R₁, R₁₃ or R₁₄are 3-chloro-2-propynyl, 3-bromo-2-propynyl, 4-chloro-2-butynyl,3-chloro-1-methyl-2-propynyl, 3-bromo-1-methyl2-propynyl,4-chloro-3-butynyl, 4-bromo-3-butynyl, 4-chloro-2-methyl3-butynyl,4-bromo-2-methyl-3-butynyl, 1-methyl-4-chloro-3-butynyl,1-methyl-4-bromo-3-butynyl, 5-chloro-4-pentynyl, 5-bromo-4-pentynyl,1-ethyl-3-chloro-2-propynyl and 1-ethyl-3-bromo-2-propynyl.

Examples of the C₂ -C₄ alkynyl group represented by R₁₂ or R₁₆ areethynyl, 1-propynyl, 2-propynyl and 1-methyl-2-propynyl.

Examples of the C₂ -C₄ haloalkynyl group represented by R₁₂ or R₁₆ arechloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-2-propynyl,3-bromo-2-propynyl, 3-iodo-2-propynyl, 1-methyl-3-chloro-2-propynyl,1-methyl-3-bromo-2-propynyl and 1-methyl-3-iodo-2-propynyl.

Examples of the C₂ -C₄ alkynyloxy group represented by R₁₂ areethynyloxy, 1-propynyloxy, 2-propynyloxy and 1-methyl-2-propynyloxy.

Examples of the C₂ -C₄ haloalkynyloxy group represented by R₁₂ arechloroethynyloxy, 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy,1-methyl-3-chloro-2-propynyloxy and 1-methyl-3-bromo-2-propynyloxy.

Examples of the C₂ -C₇ alkoxyalkyl group represented by R₁ aremethoxymethyl, 2-methoxyethyl, ethoxymethyl, isopropoxymethyl,2-propoxymethyl, 1-methoxyethyl, 2-ethoxyethyl, 1-ethoxyethyl,3-methoxypropyl, 2-methoxypropyl, 1-methoxypropyl,2-methoxy-1-methylethyl, 2-propoxyethyl, 2-ethoxypropyl,2-ethoxy-1-methylethyl, 2-methoxybutyl, 2-methoxy-1-ethylethyl,3-ethoxypropyl, 3-methoxy-n-butyl, 3-methoxy-2-methylpropyl,3-methoxy-1-methylpropyl, 2-isopropoxyethyl, 3-methoxybutyl,3-methyl-3-methoxybutyl, 2-butoxyethyl and 2-butoxy-1-methylethyl.

Examples of the C₂ -C₄ alkoxyalkyl group represented by R₁₂ aremethoxymethyl, ethoxymethyl, n-propoxymethyl, isopropoxymethyl,2-methoxyethyl, 1-methoxyethyl, 2-ethoxyethyl, 1-ethoxyethyl,3-methoxypropyl, 2-methoxypropyl, 1-methoxypropyl and2-methoxy-1-methylethyl.

Examples of the C₂ -C₇ alkylthioalkyl group represented by R₁ aremethylthiomethyl, ethylthiomethyl, 2-methylthioethyl, 1-methylthioethyl,propylthiomethyl, isopropyIthiomethyl, 2-ethylthioethyl,1-ethylthioethyl, 3-(methylthio)propyl, 2-(methylthio)propyl,1-(methylthio)propyl, 1-methyl-2-methylthioethyl, 2-isopropylthioethyl,2-(propylthio)ethyl, 2-methylthio-1-methylpropyl, 2-(methylthio)butyl,1-ethyl-2-methylthioethyl, 2-(ethylthio)propyl,2-ethylthio-1-methylethyl, 3-(ethylthio)propyl, 3-(methylthio)butyl,2-methyl-3-(methylthio)propyl, 1-methyl-3-(methylthio)propyl,2-tert-butylthioethyl, 2-isobutylthioethyl, 2-sec-butylthioethyl,3-(tert-butylthio)propyl, 3-(isobutylthio)propyl and3-(sec-butylthio)propyl.

Examples of the C₂ -C₄ alkylthioalkyl group represented by R₁₂ aremethylthiomethyl, ethylthiomethyl, propylthiomethyl,isopropylthiomethyl, 2-methylthioethyl, 1-methylthioethyl,2-ethylthioethyl, 1-ethylthioethyl, 3-methylthiopropyl,2-methylthiopropyl, 1-methylthiopropyl and 2-methylthio-1-methylethyl.

Examples of the C₃ -C₆ cycloalkyl group optionally substituted with C₁-C₄ alkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy, which is represented byR₁, are cyclopropyl, cyclobutyl, 2-methoxycyclopentyl,2-ethoxycyclopentyl, 2-propoxycyclopentyl, 2-isopropoxycyclopentyl,2-butoxycyclopentyl, 2-isobutoxycyclopentyl, 2-sec-butoxycyclopentyl,2-tert-butoxycyclopentyl, cyclopentyl, 3-methylcyclopentyl,2-methylcyclopentyl, 3-methoxycyclohexyl, 3-ethoxycyclohexyl,3-propoxycyclohexyl, 3-isopropoxycyclohexyl, 3-butoxycyclohexyl,3-isobutoxycyclohexyl, 3-sec-butoxycyclohexyl, 3-tert-butoxycyclohexyl,4-methoxycyclohexyl, 4-ethoxycyclohexyl, 4-propoxycyclohexyl,4-isopropoxycyclohexyl, 4-butoxycyclohexyl, 4-isobutoxycyclohexyl,4-sec-butoxycyclohexyl and 4-tert-butoxycyclohexyl.

Examples of the C₄ -C₉ cycloalkylalkyl group optionally substituted withC₁ -C₄ alkyl, which is represented by R₁, are cyclopropylmethyl,cyclobutylmethyl, 1-cyclopropylethyl, 2-methylcyclopropanemethyl,2-(2-methylcyclopropyl)ethyl, cyclopentylmethyl, cyclohexylmethyl,2-cyclohexylethyl, 3-cyclopentylpropyl and 3-cyclohexylpropyl.

Examples of the C₅ -C₆ cycloalkenyl group optionally substituted with C₁-C₄ alkyl, which is represented by R₁, are 2-cyclohexenyl,3,5,5-trimethyl-2-cyclohexenyl, 3-methyl-2-cyclohexenyl, 3-cyclohexenyl,2-cyclopentenyl and 3-cyclopentenyl.

Examples of the C₆ -C₈ cycloalkenylalkyl group optionally substitutedwith C₁ -C₄ alkyl, which is represented by R₁, are(1-cyclopentenyl)methyl, (3-cyclohexenyl)methyl and2-(3-cyclohexenyl)ethyl.

Examples of the C₃ -C₆ cycloalkyl group represented by R₁₂ or R₁₆ arecyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

Examples of the C₅ -C₆ cycloalkenyl group represented by R₁₂ are1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, 1-cyclohexenyl,2-cyclohexenyl and 3-cyclohexenyl.

Examples of the C₃ -C₆ cycloalkyloxy group represented by R₁₂ arecyclopropyloxy, cyclobutyloxy, cyclopentyloxy and cyclohexyloxy.

Examples of the C₅ -C₆ cycloalkenyloxy group represented by R₁₂ are1-cyclopentenyloxy, 2-cyclopentenyloxy, 3-cyclopentenyloxy,1-cyclohexenyloxy, 2-cyclohexenyloxy and 3-cyclohexenyloxy.

Examples of the C₁ -C₃ alkoxy group present in R₁ or R₁₂ are methoxy,ethoxy, n-propoxy and isopropoxy.

Examples of the C₁ -C₇ alkoxy group represented by R₁₂ are methoxy,ethoxy, 2-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy,tert-butoxy, n-pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy,(1-ethylpropyl)oxy, n-hexyloxy and n-heptyloxy.

Examples of the C₁ -C₃ haloalkoxy group represented by R₁₂ or R₁₆, orpresent in R₁₂ or R₁₆, are trifluoromethoxy, difluoromethoxy,bromodifluoromethoxy, 2-fluoroethoxy, 2,2,2-trifluoroethoxy,2-chloroethoxy, 2-bromoethoxy, 2-chloro-1,1,2-trifluoroethoxy,2-bromo-1,1,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy,1,2,2,3,3,3-hexafluoropropoxy, 3-fluoro-n-propoxy, 3-chloropropoxy,3-bromopropoxy, 2,2,3,3,3-pentafluoropropoxy, 3,3,3-trifluoropropoxy and1,1,2,2,2-pentafluoroethoxy.

Examples of the C₁ -C₃ alkylthio group represented by R₁₂ or R₁₆ aremethylthio, ethylthio, n-propylthio and isopropylthio.

Examples of the C₁ -C₃ haloalkylthio group represented by R₁₂ or R₁₆ aretrifluoromethylthio, difluoromethylthio, bromodifluoromethylthio,2,2,2-trifluoroethyl-thio, 2-chloro-1,1,2-trifluoroethylthio,2-bromo-1,1,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio,2-chloroethylthio, 2-fluoroethylthio, 2-bromoethylthio,3-fluoropropylthio, 3-chloro-n-propylthio, (3-bromopropyl)thio,2,2,3,3,3-pentafluoropropylthio and 3,3,3-trifluoropropylthio.

Examples of the C₃ -C₆ alkenylthio group represented by R₁₂ areallyloxy, 2-methylallyloxy, 2-butenyloxy, 3-methyl-2-butenyloxy,2-methyl-2-butenyloxy, 2-pentenyloxy and 2-hexenyloxy.

Examples of the C₃ -C₆ haloalkenyloxy group represented by R₁₂ are3,3-dichloroallyloxy, 3,3-dibromoallyloxy, 2,3-dichloroallyloxy,2,3-dibromoallyloxy, 2-chloro-2-propenyloxy, 3-chloro-2-propenyloxy,2-bromo-2-propenyloxy and 3-chloro-2-butenyloxy.

Examples of the C₁ -C₃ hydroxyalkyl group represented by R₁₂ arehydroxymethyl, 2-hydroxyethyl, 1-hydroxyethyl, 3-hydroxypropyl,2-hydroxypropyl and 1-hydroxypropyl.

Examples of the C₂ -C₅ alkoxycarbonyl group represented by R₁₂ aremethoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl,n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl andtert-butoxycarbonyl.

Examples of the C₁ -C₄ alkyl group represented by R₁₆, or present in R₁,R₁₂ or R₁₆, are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,sec-butyl and tert-butyl.

Examples of the C₁ -C₄ alkoxy group represented by R₁₆, or present inR₁₆, are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy,isobutoxy and tert-butoxy.

Examples of the C₁ -C₂ alkylsulfinyl group represented by R₁₆ aremethylsulfinyl and ethylsulfinyl.

Examples of the C₁ -C₂ alkylsulfonyl group represented by R₁₆ aremethylsulfonyl and ethylsulfonyl.

Examples of the C₁ -C₂ haloalkylsulfinyl group represented by R₁₆ aretrifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl andperfluoroethylsulfinyl.

Examples of the C₁ -C₂ haloalkylsulfonyl group represented by R₁₆ aretrifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl andperfluoroethylsulfonyl.

Examples of the (C₁ -C₂ alkyl)aminocarbonyl group represented by R₁₆ aremethylaminocarbonyl and ethylaminocarbonyl.

Examples of the [di(C₁ -C₂ alkyl)amino]carbonyl group represented by R₁₆are dimethylaminocarbonyl, N-methyl-N-ethylaminocarbonyl anddiethylaminocarbonyl.

Examples of the heterocyclic ring in the optionally substitutedheterocyclic group represented by R₁ are hexamethylenimine,heptamethylenimine, 5- and 6-membered heterocyclic rings containing atleast one oxygen, sulfur or nitrogen atom. Specific examples thereofinclude isoxazole, isothiazole, thiazole, 1,3,4-thiadiazole, pyrrole,furan, thiophene, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole,1,2,3,4-tetrazole, pyridine, pyridazine, pyrimidine, pyrazine,1,2,4-triazine, 1,3,5-triazine, indole, benzodioxane, pyrrolidine,2,3-dihydro-4H-pyran-4-one, chromone, morpholine, 2-pyrroline,3-pyrroline, 1,2,3,6-tetrahydropyrrolidine, piperazine, thiomorpholine,thiazolidine, benzofuran, thianaphthalene, imidazole, benzimidazole,benzotriazole, benzisoxazole, benzoxazole, benzothiazole, quinoline,isoquinoline, quinoxaline, quinazole, piperidine, piperazine,tetrahydrofuran, tetrahydropyran and pyrazoline.

The following are preferred examples of the present compounds:

dihalopropene compounds wherein R₁₃ and R₁₄ are independently hydrogenor C₁ -C₃ alkyl;

dihalopropene compounds wherein R₁ is C₁ -C₁₀ alkyl, C₁ -C₅ haloalkyl,C₂ -C₁₀ alkenyl, C₂ -C₆ haloalkenyl, C₃ -C₉ alkynyl or C₃ -C₅haloalkynyl;

dihalopropene compounds wherein L is C(═W)NR₁₃ ;

dihalopropene compounds wherein L is WC(═W₁)NR₁₃ ;

dihalopropene compounds wherein R₁ is Q₁, Q₂, Q₃ or Q₄ ;

dihalopropene compounds wherein R₁ is Q₁ ;

dihalopropene compounds wherein R₁ is Q₁, and L is C═W, C(═W)NR₁₃ or SO₂NR₁₃ ;

dihalopropene compounds wherein R₁ is Q₁, and L is C(═W)NR₁₃ or SO₂ NR₁₃;

dihalopropene compounds wherein R₁ is Q₁, and L is C(═W)NR₁₃ ;

dihalopropene compounds wherein R₁ is Q₁ in which p=0, and L is C═W,C(═W)NR₁₃ or SO₂ NR₁₃ ;

dihalopropene compounds wherein R₁ is Q₁ in which p=0, and L isC(═W)NR₁₃ or SO₂ NR₁₃ ;

dihalopropene compounds wherein R₁ is Q₁, in which p=0, and L isC(═W)NR₁₃ ;

dihalopropene compounds wherein R₂, R₃ and R₄ are independently halogenor C₁ -C₃ alkyl;

dihalopropene compounds wherein R₂ and R₃ are both chlorine, and R₄ ishydrogen;

dihalopropene compounds wherein Y and Z are both oxygen;

dihalopropene compounds wherein R₅, R₆ and R₇ are independently hydrogenor C₁ -C₃ alkyl; and

dihalopropene compounds wherein R₅, R₆ and R₇ are all hydrogen.

The following are other preferred examples of the present compounds:

dihalopropene compounds wherein R₁ is a 5- or 6-membered heterocyclicgroup containing at least one oxygen, sulfur or nitrogen atom andoptionally substituted with (R₁₆)_(s) ; and more particularly,

dihalopropene compounds wherein the 5- or 6-membered heterocyclic groupis 2-pyridyl, 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 3-pyridyl,4-pyridyl, 2-thienyl, 3-thienyl, 2-furyl or 3-furyl;

dihalopropene compounds wherein the 5- or 6-membered heterocyclic groupis 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrazinyl, 2-indolyl,2-pyrrolyl, 2-quinolyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, and L is C═W,C(═W)NR₁₃ or SO₂ NR₁₃ ;

dihalopropene compounds wherein the 5- or 6-membered heterocyclic groupis 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrazinyl, 2-indolyl,2-pyrrolyl, 2-quinolyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, and L isC(═W)NR₁₃ or SO₂ NR₁₃ ;

dihalopropene compounds wherein the 5- or 6-membered heterocyclic groupis 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrazinyl, 2-indolyl,2-pyrrolyl, 2-quinolyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, and L isC(═W)NR₁₃ ; and

dihalopropene compounds wherein the 5- or 6-membered heterocyclic groupis 1-pyrrolidinyl or 1-piperidyl, and L is C═W.

The present compounds can be produced, for example, by the followingproduction processes A-N.

(Production Process A)

In this process, a compound of the general formula: ##STR6## wherein R₁,R₂, R₃, R₄, R₅, R₆, R₇, L, Y, Z, m and n are each as defined above, isreacted with a compound of the general formula:

    L.sub.2 --CH.sub.2 CH═CX.sub.2                         [VI]

wherein X is as defined above, and L₂ is halogen (e.g., chlorine,bromine, iodine), mesyloxy or tosyloxy.

The reaction is preferably effected in an inert solvent in the presenceof a suitable base.

Examples of the solvent which can be used are ketones such as acetone,methyl ethyl ketone and cyclohexanone; ethers such as1,2-dimethoxyethane, tetrahydrofuran, dioxane and dialkyl (e.g., C₁ -C₄)ether (e.g., diethyl ether, diisopropyl ether); N,N-dimethylformamide,dimethylsulfoxide, hexamethylphosphoric triamide, sulforane,acetonitrile, nitromethane; halogenated hydrocarbons such asdichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene;hydrocarbons such as toluene, benzene and xylene; and water. Ifnecessary, a mixture of these solvents can be used.

Examples of the base which can be used are hydroxides of alkali metalsor alkaline earth metals, such as lithium hydroxide, sodium hydroxide,potassium hydroxide and calcium hydroxide; carbonates of alkali metalsor alkaline earth metals, such as lithium carbonate, potassiumcarbonate, sodium carbonate and calcium carbonate; hydrides of alkalimetals or alkaline earth metals, such as lithium hydride, sodiumhydride, potassium hydride and calcium hydride; alkali metal alkoxides(e.g., C₁ -C₄), such as sodium methoxide, sodium ethoxide and potassiumtert-butoxide; and organic bases such as triethylamine and pyridine. Ifnecessary, catalysts such as ammonium salts (e.g.,benzyltriethylammonium chloride) may be added to the reaction system ata ratio of 0.01 to 1 mole per mole of the compound of general formula[V].

The reaction temperature is usually set within the range of -20° C. to+150° C. or the boiling point of a solvent used in the reaction,preferably -5° C. to +100° C. or the boiling point of a solvent used inthe reaction.

The molar ratio of the starting materials and bases to be used in thereaction can be freely determined, but it is favorable to effect thereaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification may be carried out, if necessary, by anordinary technique such as chromatography, distillation orrecrystallization.

(Production Process B for the Present Compounds wherein Y is Oxygen)

In this process, a compound of general formula [V] is reacted with analcohol compound of the general formula:

    HO--CH.sub.2 CH═CX.sub.2                               [VII]

wherein X is as defined above.

The reaction is preferably effected in the presence of a suitabledehydrating agent in an inert solvent, if necessary.

Examples of the dehydrating agent which can be used aredicyclohexylcarbodiimide, and dialkyl(e.g., C₁ -C₄)azodicarboxylates(e.g., diethylazodicarboxylate,diisopropylazodicarboxylate)-trialkyl(e.g., C₁ -C₂₀)phosphine ortriarylphosphine (e.g., triphenylphosphine, trioctylphosphine,tributylphosphine).

Examples of the solvent which can be used are hydrocarbons such asbenzene, xylene and toluene; ethers such as diethyl ether, diisopropylether, tetrahydrofuran and dioxane; and halogenated hydrocarbons such ascarbon tetrachloride, dichloromethane, chlorobenzene anddichlorobenzene.

The reaction temperature is usually set within the range of -20° C. to+200° C. or the boiling point of a solvent used in the reaction.

The molar ratio of the starting materials and dehydrating agents to beused in the reaction can be freely determined, but it is favorable toeffect the reaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification may be carried out, if necessary, by anordinary technique such as chromatography, distillation orrecrystallization.

(Production Process C for the Present Compounds wherein Y is Oxygen)

In this process, an aldehyde compound of the general formula: ##STR7##wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇, L, Z, m and n are each as definedabove, is reacted with carbon tetrachloride or carbon tetrabromide.

The reaction is preferably effected in the presence of a suitabletrialkylphosphine or triarylphosphine, and if necessary, in the presenceof metal zinc, in an inert solvent.

Examples of the solvent which can be used are hydrocarbons such asbenzene, xylene and toluene; ethers such as diethyl ether, diisopropylether, tetrahydrofuran and dioxane; and halogenated hydrocarbons(exclusive of carbon tetrabromide and carbon tetrachloride) such asdichloromethane, 1,2-dichloroethane and chlorobenzene.

The reaction temperature is usually set within the range of -30° C. to+150° C. or the boiling point of a solvent used in the reaction.

Examples of the trialkyl(e.g., C₁ -C₂₀)phosphine or triarylphosphine,which can be used in the reaction, are triphenylphosphine andtrioctylphosphine. The metal zinc which is used, if necessary, ispreferably in dust form.

The molar ratio of the starting materials and reagents to be used in thereaction can be freely determined, but the ratio is preferably such thatcarbon tetrabromide or tetrachloride, trialkylphosphine ortriarylphosphine, and zinc are 2 moles, 2 or 4 moles (2 moles when zincis used), and 2 moles, respectively, per mole of the aldehyde compoundof general formula [VIII], or it is favorable to effect the reaction ata ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification may be carried out, if necessary, by anordinary technique such as chromatography, distillation orrecrystallization.

(Production Process D for the Present Compounds wherein Y and Z are bothOxygen)

In this process, a compound of the general formula: ##STR8## wherein R₂,R₃, R₄, X and n are each as defined above, is reacted with a compound ofthe general formula: ##STR9## wherein R₁, R₅, R₆, R₇, L, L₂ and m areeach as defined above.

The reaction is preferably effected in the presence of a suitable basein an inert solvent.

Examples of the solvent which can be used are ketones such as acetone,methyl ethyl ketone and cyclohexanone; ethers such as1,2-dimethoxyethane, tetrahydrofuran, dioxane and dialkyl (e.g., C₁ -C₄)ethers (e.g., diethyl ether, diisopropyl ether); N,N-dimethylformamide,dimethylsulfoxide, hexamethylphosphoric triamide, sulforane,acetonitrile, nitromethane; halogenated hydrocarbons such asdichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene;hydrocarbons such as toluene, benzene and xylene; and water. Ifnecessary, a mixture of these solvents can be used.

Examples of the base which can be used are hydroxides of alkali metalsor alkaline earth metals, such as lithium hydroxide, sodium hydroxide,potassium hydroxide and calcium hydroxide; carbonates of alkali metalsor alkaline earth metals, such as lithium carbonate, potassiumcarbonate, sodium carbonate and calcium carbonate; hydrides of alkalimetals or alkaline earth metals, such as lithium hydride, sodiumhydride, potassium hydride and calcium hydride; alkali metal alkoxides(e.g., C₁ -C₄) such as sodium methoxide, sodium ethoxide and potassiumtert-butoxide; organic bases such as triethylamine and pyridine. Ifnecessary, catalysts such as ammonium salts (e.g.,benzyltriethylammonium chloride) may be added to the reaction system ata ratio of 0.01 to 1 mole per mole of the compound of general formula[IX].

The reaction temperature is usually set within the range of -20° C. to+150° C. or the boiling point of a solvent used in the reaction,preferably -5° C. to +100° C. or the boiling point of a solvent used inthe reaction.

The molar ratio of the starting materials and dehydrating agents to beused in the reaction can be freely determined, but it is favorable toeffect the reaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification may be carried out, if necessary, by anordinary technique such as chromatography, distillation orrecrystallization.

(Production Process E for the Present Compounds wherein Y and Z are bothOxygen)

In this process, a compound of general formula [IX] is reacted with acompound of the general formula: ##STR10## wherein R₁, R₅, R₆, R₇, L andm are as defined above.

The reaction is preferably effected in the presence of a suitabledehydrating agent in an inert solvent, if necessary.

Examples of the dehydrating agent which can be used aredicyclohexylcarbodiimide, and dialkyl(e.g., C₁ -C₄)azodicarboxylates(e.g., diethylazodicarboxylate,diisopropylazodicarboxylate)-trialkyl(e.g., C₁ -C₂₀)phosphine ortriarylphosphine (e.g., triphenylphosphine, trioctylphosphine,tributylphosphine).

Examples of the solvent which can be used are hydrocarbons such asbenzene, xylene and toluene; ethers such as diethyl ether, diisopropylether, tetrahydrofuran and dioxane; and halogenated hydrocarbons such ascarbon tetrachloride, dichloromethane, chlorobenzene anddichlorobenzene.

The reaction temperature is usually set within the range of -20° C. to+200° C. or the boiling point of a solvent used in the reaction.

The molar ratio of the materials and dehydrating agents to be used inthe reaction can be freely determined, but it is favorable to effect thereaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification may be carried out, if necessary, by anordinary technique such as chromatography, distillation orrecrystallization.

(Production Process F for the Present Compounds wherein L is--C(═O)--NR₁₃ --)

In this process, an amine compound of the general formula: ##STR11##wherein R₂, R₃, R₄, R₅, R₆, R₇, R₁₃, X, Y, Z, m and n are each asdefined above, is reacted with a carboxylic acid compound of the generalformula:

    R.sub.1 --C(═O)--V                                     [XIII]

wherein R₁ is as defined above, and V is chlorine, bromine, hydroxyl,methoxy, ethoxy, propoxy or 1-imidazolyl.

(i) In the case where V in general formula [XIII] is chlorine, bromineor 1-imidazolyl, examples of the reaction solvent which can be used areethers such as diethyl ether, tetrahydrofuran and dioxane; aromatichydrocarbons such as benzene, toluene, xylene, chlorobenzene andpyridine; hydrocarbons such as n-hexane, n-heptane and cyclohexane;halogenated hydrocarbons such as methylene chloride, chloroform, carbontetrachloride and 1,2-dichloroethane; esters such as ethyl acetate andmethyl acetate; water; nitriles such as acetonitrile; polar solventssuch as N,N-dimethylformamide, N,N-dimethylacetamide,N-methylpyrrolidone and dimethylsulfoxide; and mixtures thereof.

The reaction temperature is usually set within the range of -20° C. to+150° C. or the boiling point of a solvent used in the reaction,preferably 0° C. to 50° C.

The reaction is usually effected in the presence of a base such assodium hydroxide, potassium hydroxide, sodium carbonate, potassiumcarbonate, triethylamine or pyridine at a ratio of 1 to 10 moles permole of the compound of general formula [XIII].

When two phase reaction is effected with water as a solvent, the use ofa phase transfer catalyst such as tetra-n-butylammonium bromide orbenzyltriethylammonium chloride makes it possible to raise the reactionrate.

(ii) In the case where V in general formula [XIII] is hydroxyl, methoxy,ethoxy or propoxy, the reaction is usually effected without any solvent,or in a polar solvent such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylpyrrolidone or dimethylsulfoxide, or inan aromatic hydrocarbon solvent such as benzene, toluene, xylene orchlorobenzene, at a reaction temperature of 50° to 250° C.

If necessary, as a reaction catalyst, an acidic substance such assulfuric acid, benzenesulfonic acid, p-toluenesulfonic acid or activesilica gel, or a basic substance such as pyridine, triethylamine, sodiummethoxide, sodium ethoxide or active alumina can be used at a weightwhich is 0.0001 to 1 time as much as the weight of the carboxylic acidcompound of general formula [XIII].

The molar ratio of the materials and dehydrating agents to be used inthe reaction can be freely determined, but it is favorable to effect thereaction at an equimolar ratio or a ratio closer thereto.

(iii) In the case where V in general formula [XIII] is hydroxyl, thefollowing process can be used in the production.

That is, a carboxylic acid compound of general formula [XIII] is usuallyreacted with an amine compound of general formula [XII] in the presenceof an inert organic solvent or without any solvent, thereby causingcondensation by dehydration to give the desired compound of the presentinvention. Examples of the dehydrating agent are carbodiimides such asdicyclohexylcarbodiimide and1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; and inorganic dehydratingagents such as silicon tetrachloride. Examples of the inert organicsolvent are non-aromatic hydrocarbons such as n-pentane, n-hexane,n-heptane and cyclohexane; aromatic hydrocarbons such as benzene,toluene and xylene; chlorinated hydrocarbons such as methylene chloride,chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene ando-dichlorobenzene; esters such as ethyl acetate and methyl acetate;amides such as N,N-dimethylformamide, N,N-dimethylacetamide andN-methylpyrrolidone; nitriles such as acetonitrile; ethers such asdiethyl ether, tetrahydrofuran and dioxane; and pyridine.

The reaction temperature is usually set within the range of -20° C. to+150° C. or the boiling point of a solvent used in the reaction.

The molar ratio of the materials and dehydrating agents to be used inthe reaction can be freely determined, but it is favorable to effect thereaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction in case (i), (ii) or (iii), thereaction mixture is subjected to ordinary post-treatments such asorganic solvent extraction and concentration, and the desired compoundof the present invention can be isolated. Further, purification may becarried out, if necessary, by an ordinary technique such aschromatography, distillation or recrystallization.

(Production Process G for the Present Compounds wherein L is --NR₁₃--C--(═O)--)

In this process, a compound of the general formula: ##STR12## whereinR₂, R₃, R₄, R₅, R₆, R₇, X, Y, Z, V, m and n are each as defined above,is reacted with a compound of the general formula:

    R.sub.1 --NH--R.sub.13 or R.sub.20 --H                     [XV]

wherein R₁ and R₁₃ are each as defined above, and R₂₀ -H is a 5- or6-membered heterocyclic group optionally substituted with (R₁₆)_(s)containing an NH moiety, or a 5- or 6-membered heterocyclic groupcontaining at least one oxygen, sulfur or nitrogen atom and optionallysubstituted with (R₁₆)_(s) containing an NH moiety (e.g., pyrrole,piperidine, 2,6-dihydropyrrole, morpholine), in which (R₁₆)_(s) is asdefined above.

(i) In the case where V in general formula [XIV] is chlorine, bromine or1-imidazolyl, examples of the reaction solvent which can be used areethers such as diethyl ether, tetrahydrofuran and dioxane; aromatichydrocarbons such as benzene, toluene, xylene, chlorobenzene andpyridine; hydrocarbons such as n-hexane, n-heptane and cyclohexane;halogenated hydrocarbons such as methylene chloride, chloroform, carbontetrachloride and 1,2-dichloroethane; esters such as ethyl acetate andmethyl acetate; water; nitriles such as acetonitrile; polar solventssuch as N,N-dimethylformamide, N,N-dimethylacetamide,N-methylpyrrolidone and dimethylsulfoxide; and mixtures thereof.

The reaction temperature is usually set within the range of -20° C. to+150° C. or the boiling point of a solvent used in the reaction,preferably 0° C. to 50° C.

The reaction is usually effected in the presence of a base such assodium hydroxide, potassium hydroxide, sodium carbonate, potassiumcarbonate, triethylamine or pyridine at a ratio of 1 to 10 moles permole of the compound of general formula [XIV].

When two phase reaction is effected with water as a solvent, the use ofa phase transfer catalyst such as tetra-n-butylammonium bromide orbenzyltriethylammonium chloride makes it possible to raise the reactionrate.

(ii) In the case where V in general formula [XIV] is hydroxyl, methoxy,ethoxy or propoxy, the reaction is usually effected without any solvent,or in a polar solvent such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylpyrrolidone or dimethylsulfoxide, or inan aromatic hydrocarbon solvent such as benzene, toluene, xylene, orchlorobenzene, at a reaction temperature of 50° to 250° C.

If necessary, as a reaction catalyst, an acidic substance such assulfuric acid, benzenesulfonic acid, p-toluenesulfonic acid or activesilica gel, or a basic substance such as pyridine, triethylamine, sodiummethoxide, sodium ethoxide or active alumina can be used at a weightwhich is 0.0001 to 1 time as much as the weight of the carboxylic acidcompound of general formula [XIV].

The molar ratio of the materials to be used in the reaction can befreely determined, but it is favorable to effect the reaction at anequimolar ratio or a ratio closer thereto.

(iii) In the case where V in general formula [XIV] is hydroxyl, thefollowing process can be used in the production.

That is, a compound of general formula [XIV] is usually reacted with anamine compound of general formula [XV] in the presence of an inertorganic solvent or without any solvent, thereby causing condensation bydehydration to give the desired compound of the present invention.Examples of the dehydrating agent are carbodiimides such asdicyclohexylcarbodiimide and1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; and inorganic dehydratingagents such as silicon tetrachloride. Examples of the inert organicsolvent are non-aromatic hydrocarbons such as n-pentane, n-hexane,n-heptane and cyclohexane; aromatic hydrocarbons such as benzene,toluene, xylene, chlorobenzene, pyridine and o-dichlorobenzene;chlorinated hydrocarbons such as methylene chloride, chloroform, carbontetrachloride and 1,2-dichloroethane; esters such as ethyl acetate andmethyl acetate; amides such as N,N-dimethylformamide,N,N-dimethylacetamide and N-methylpyrrolidone; nitrites such asacetonitrile; and ethers such as diethyl ether, tetrahydrofuran anddioxane.

The reaction temperature is usually set within the range of -20° C. to+150° C. or the boiling point of a solvent used in the reaction.

The molar ratio of the materials and dehydrating agents to be used inthe reaction can be freely determined, but it is favorable to effect thereaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction in case (i), (ii) or (iii), thereaction mixture is subjected to ordinary post-treatments such asorganic solvent extraction and concentration, and the desired compoundof the present invention can be isolated. Further, purification may becarried out, if necessary, by an ordinary technique such aschromatography, distillation or recrystallization.

(Production Process H for the Present Compounds wherein L is--C(═S)--NR₁₃ -- or --NR₁₃ --C(═S)--)

In this process, the present compounds wherein L is --C(═O)--NR₁₃ -- or--NR₁₃ --C(═O)-- are reacted with phosphorus pentasulfide or theLawesson's Reagent.

Examples of the solvent which can be used are aromatic hydrocarbons suchas benzene, toluene, xylene, chlorobenzene, pyridine and quinoline. Ifnecessary, a mixture of these solvents can be used.

The reaction temperature is usually set within the range of 0° C. to150° C. or the boiling point of a solvent used in the reaction,preferably 20° C. to 150° C. or the boiling point of a solvent used inthe reaction.

The molar ratio of the starting materials to be used in the reaction canbe freely determined, but it is preferred that phosphorus pentasulfideor the Lawesson's Reagent is used at a ratio of 0.2 to 20 moles or 0.5to 50 moles, respectively, per mole of the present compounds wherein Lis --C(═O)--NR₁₃ -- or --NR₁₃ --C(═O)--.

(Production Process I for the Present Compounds wherein L is --SO₂--NR₁₃ --)

In this process, an amine compound of general formula [XII] is reactedwith a sulfonic acid compound of the general formula:

    R.sub.1 --SO.sub.2 --L.sub.3                               [XVI]

wherein R₁ is as defined above, and L₃ is chlorine or bromine.

Examples of the solvent which can be used are ethers such as diethylether, tetrahydrofuran and dioxane; aromatic hydrocarbons such asbenzene, toluene, xylene, chlorobenzene and pyridine; hydrocarbons suchas n-hexane, n-heptane and cyclohexane; halogenated hydrocarbons such asmethylene chloride, chloroform, carbon tetrachloride and1,2-dichloroethane; esters such as ethyl acetate and methyl acetate;water; nitrites such as acetonitrile; polar solvents such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone anddimethylsulfoxide; and mixtures thereof.

The reaction temperature is usually set within the range of -20° C. to+150° C. or the boiling point of a solvent used in the reaction,preferably 0° C. to 50° C.

The reaction is usually effected in the presence of a base, such assodium hydroxide, potassium hydroxide, sodium carbonate, potassiumcarbonate, triethylamine or pyridine, at a ratio of 1 to 10 moles permole of the compound of general formula [XVI].

When two phase reaction is effected with water as a solvent, the use ofa phase transfer catalyst such as tetra-n-butylammonium bromide orbenzyltriethylammonium chloride makes it possible to raise the reactionrate.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification may be carried out, if necessary, by anordinary technique such as chromatography, distillation orrecrystallization.

(Production Process J for the Present Compounds wherein L is --NR₁₃--SO₂ --)

In this process, a sulfonic acid compound of the general formula:##STR13## wherein R₂, R₃, R₄, R₅, R₆, R₇, X, Y, Z, L₃, m and n are eachas defined above, is reacted with the compound of general formula [XV].

Examples of the solvent which can be used are ethers such as diethylether, tetrahydrofuran and dioxane; aromatic hydrocarbons such asbenzene, toluene, xylene, chlorobenzene and pyridine; hydrocarbons suchas n-hexane, n-heptane and cyclohexane; halogenated hydrocarbons such asmethylene chloride, chloroform, carbon tetrachloride and1,2-dichloroethane; esters such as ethyl acetate and methyl acetate;water; nitriles such as acetonitrile; polar solvents such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone anddimethylsulfoxide; and mixtures thereof.

The reaction temperature is usually set within the range of -20° C. to+150° C. or the boiling point of a solvent used in the reaction,preferably 0° C. to 50° C.

The reaction is usually effected in the presence of a base, such assodium hydroxide, potassium hydroxide, sodium carbonate, potassiumcarbonate, triethylamine or pyridine, at a ratio of 1 to 10 moles permole of the compound of general formula [XVII].

When two phase reaction is effected with water as a solvent, the use ofa phase transfer catalyst such as tetra-n-butylammonium bromide orbenzyltriethylammonium chloride makes it possible to raise the reactionrate.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification may be carried out, if necessary, by anordinary technique such as chromatography, distillation orrecrystallization.

(Production Process K for the Present Compounds wherein L is --NR₁₃--C(═W₁)W--)

(The First Step of Production Process K)

In this process, a compound of the general formula: ##STR14## whereinR₂, R₃, R₄, R₅, R₆, R₇, W, X, Y, Z, m and n are each as defined above,is reacted with a (thio)isocyanate compound of the general formula:

    R.sub.1 --N═C═W.sub.1                              [XIX]

wherein R₁ and W₁ are each as defined above, to give a carbamic acidderivative of the general formula: ##STR15## wherein R₁, R₂, R₃, R₄, R₅,R₆, R₇, W, W₁, X, Y, Z, m and n are each as defined above.

The reaction is preferably effected, if necessary, in the presence of anappropriate catalyst in a solvent having no influence thereon.

Examples of the solvent which can be used are hydrocarbons such asbenzene and toluene; ethers such as diethyl ether, tetrahydrofuran anddioxane; polar solvents such as N,N-dimethylformamide, dimethylsulfoxideand hexamethylphosphoric acid triamide; halogenated hydrocarbons such asmethylene chloride, chloroform, 1,2-dichloroethane and chlorobenzene;acetonitrile; and nitromethane. If necessary, a mixture of thesesolvents can be used.

Examples of the catalyst which can be used are organic bases such astriethylamine, pyridine and sodium acetate; and acids such as aluminumchloride, hydrogen chloride and boron trifluoride-ether complex (BF₃--(C₂ H₅)₂ O).

The reaction temperature is usually set within the range of -20° C. tothe boiling point of a solvent used in the reaction, preferably -5° C.to the boiling point of a solvent used in the reaction.

The molar ratio of the materials to be used in the reaction can befreely determined, but it is favorable to effect the reaction at anequimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention(wherein R₁₃ is H) can be isolated. Further, purification may be carriedout, if necessary, by an ordinary technique such as chromatography,distillation or recrystallization.

(The Second Step of Production Process K)

In this process, a carbamic acid derivative of general formula [XX] isreacted with a halogenated compound of the general formula:

    R.sub.13 --L.sub.4                                         [XXI]

wherein R₁₃ is as defined above (however, it does not representhydrogen) and L₄ is halogen (e.g., chlorine, bromine, iodine), to givethe present compounds (wherein R₁₃ is not hydrogen).

The reaction is preferably effected in the presence of an appropriatecatalyst in a solvent having no influence thereon.

Examples of the solvent which can be used are ketones such as acetoneand methyl ethyl ketone; hydrocarbons such as benzene and toluene;ethers such as diethyl ether, tetrahydrofuran and dioxane; halogenatedhydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethaneand chlorobenzene; acetonitrile; nitromethane; and pyridine. Ifnecessary, a mixture of these solvents can be used.

Examples of the base which can be used are carbonates of alkali metals,such as potassium carbonate; hydrides of alkali metals, such as sodiumhydride; and organic bases such as sodium methoxide, sodium ethoxide,triethylamine and pyridine.

The reaction temperature is usually set within the range of -10° C. tothe boiling point of a solvent used in the reaction.

The molar ratio of the materials to be used in the reaction can befreely determined, but it is preferred that the halogenated compound ofgeneral formula [XXI] and the base are used at ratios of 1 to 2 molesand 0.9 to 20 moles, respectively, per mole of the carbamic acidderivative of general formula [XX].

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification may be carried out, if necessary, by anordinary technique such as chromatography, distillation orrecrystallization.

(Production Process L for the Present Compounds wherein L is--WC(═W₁)--NR₁₃ --)

In this process, an amine compound of general formula [XII] is reactedwith a compound of the general formula:

    R.sub.1 --W--C(═W.sub.1)--L.sub.3                      [XXII]

wherein R₁, W, W₁ and L₃ are each as defined above.

The reaction is preferably effected in the presence of an appropriatecatalyst in a solvent having no influence thereon.

Examples of the base which can be used are carbonates of alkali metals,such as potassium carbonate; and organic bases such as triethylamine andpyridine. If necessary, a catalyst such as ammonium salts (e.g.,benzyltriethylammonium chloride) may be added to the reaction system.

Examples of the solvent which can be used are ketones such as acetoneand methyl ethyl ketone; hydrocarbons such as benzene and toluene;ethers such as diethyl ether, tetrahydrofuran and dioxane; halogenatedhydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethaneand chlorobenzene; acetonitrile; and nitromethane. If necessary, amixture of these solvents or a mixture of these solvents and water canbe used.

The reaction temperature is usually set within the range of -20° C. tothe boiling point of a solvent used in the reaction, preferably -5° C.to the boiling point of a solvent used in the reaction.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification may be carried out, if necessary, by anordinary technique such as chromatography, distillation orrecrystallization.

(Production Process M for the Present Compounds wherein L is --NR₁₄--C(═W)NR₁₃ --)

(The First Step of Production Process M)

In this process, an amine compound of general formula [XII] is reactedwith a (thio)isocyanate compound of general formula [XIX] to give anurea derivative compound of the general formula: ##STR16## wherein R₁,R₂, R₃, R₄, R₅, R₆, R₇, R₁₃, W, X, Y, Z, m and n are each as definedabove.

Examples of the solvent which can be used are hydrocarbons such asbenzene and toluene; ethers such as diethyl ether, tetrahydrofuran anddioxane; polar solvents such as N,N-dimethylformamide, dimethylsulfoxideand hexamethylphosphoric acid triamide; halogenated hydrocarbons such asmethylene chloride, chloroform, 1,2-dichloroethane and chlorobenzene;acetonitrile; and nitromethane. If necessary, a mixture of thesesolvents can be used.

The reaction temperature is usually set within the range of -20° C. tothe boiling point of a solvent used in the reaction, preferably -5° C.to the boiling point of a solvent used in the reaction.

The molar ratio of the materials to be used in the reaction can befreely determined, but it is favorable to effect the reaction at anequimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention(wherein R₁₄ is H) can be isolated. Further, purification may be carriedout, if necessary, by an ordinary technique such as chromatography,distillation or recrystallization.

(The Second Step of Production Process M)

In this process, an urea derivative compound of general formula [XXIII]is reacted with a compound of the general formula:

    R.sub.14 --L.sub.4                                         [XXIV]

wherein R₁₄ and L₄ are each as defined above, to give the presentcompounds (wherein R₁₄ is not hydrogen).

The reaction is preferably effected in the presence of an appropriatecatalyst in a solvent having no influence thereon.

Examples of the solvent which can be used are ketones such as acetoneand methyl ethyl ketone; hydrocarbons such as benzene and toluene;ethers such as diethyl ether, tetrahydrofuran and dioxane; halogenatedhydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethaneand chlorobenzene; acetonitrile; nitromethane; and pyridine. Ifnecessary, a mixture of these solvents can be used.

Examples of the base which can be used are carbonates of alkali metals,such as potassium carbonate; hydrides of alkali metals, such as sodiumhydride; and organic bases such as sodium methoxide, sodium ethoxide,triethylamine and pyridine.

The reaction temperature is usually set within the range of -10° C. tothe boiling point of a solvent used in the reaction.

The molar ratio of the materials to be used in the reaction can befreely determined, but it is preferred that the compound of generalformula [XXIV] and the base are used at ratios of 1 to 2 moles and 0.9to 20 moles, respectively, per mole of the urea derivative compound ofgeneral formula [XXIII].

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification may be carried out, if necessary, by anordinary technique such as chromatography, distillation orrecrystallization.

When any one of the present compounds has an asymmetric carbon atom, itis to be construed to include its optically active isomers (i.e.,(+)-form and (-)-form) having biological activity and their mixtures atany ratio. When any one of the present compounds exhibits geometricalisomerism, it is to be construed to include its geometrical isomers(i.e., cis-form and trans-form) and their mixtures at any ratio.

The following are specific examples of the present compounds; however,the present invention is not limited to these examples. ##STR17## (inwhich R₁ is as defined in Tables 1 to 7).

                  TABLE 1                                                         ______________________________________                                        R.sup.1            R.sup.1                                                    ______________________________________                                        CH.sub.3 --        (CH.sub.3).sub.2 CHCH.sub.2 CH(CH.sub.3)--                   C.sub.2 H.sub.5 -- CH.sub.3 (CH.sub.2).sub.5 CH(CH.sub.3)--                   CH.sub.3 CH.sub.2 CH.sub.2 -- CH.sub.3 (CH.sub.2).sub.6 CH(CH.sub.3)                            (CH.sub.3).sub.2 CH-- CF.sub.3 --                           CH.sub.3 (CH.sub.2).sub.2 CH.sub.2 -- CF.sub.2 H--                            (CH.sub.3).sub.2 CHCH.sub.2 -- CF.sub.2 Br--                                  CH.sub.3 CH.sub.2 CH(CH.sub.3)-- CF.sub.3 CH.sub.2 --                         (CH.sub.3).sub.3 C-- CF.sub.3 CF.sub.2 --                                     CH.sub.3 (CH.sub.2).sub.3 CH.sub.2 -- FCH.sub.2 CH.sub.2 --                   (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 -- ClCH.sub.2 CH.sub.2 --                (CH.sub.3).sub.3 CCH.sub.2 -- BrCH.sub.2 CH.sub.2 --                          CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2 -- ICH.sub.2 CH.sub.2 --                  CH.sub.3 (CH.sub.2).sub.4 CH.sub.2 -- (Cl).sub.2 CHCH.sub.2 --                (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 -- BrCF.sub.2 CF.sub.2 --       CH.sub.3 (CH.sub.2).sub.5 CH.sub.2 -- CF.sub.2 HCF.sub.2 --                   CH.sub.3 (CH.sub.2).sub.6 CH.sub.2 -- CFClHCF.sub.2 --                        CH.sub.3 (CH.sub.2).sub.7 CH.sub.2 -- CF.sub.2 BrCFH--                        CH.sub.3 (CH.sub.2).sub.8 CH.sub.2 -- ClCH.sub.2 CH.sub.2 CH.sub.2 --                           (C.sub.2 H.sub.5).sub.2 CH-- BrCH.sub.2 CH.sub.2                             CH.sub.2 --                                                  (C.sub.2 H.sub.5).sub.2 CHCH.sub.2 -- FCH.sub.2 CH.sub.2 CH.sub.2 --                            CH.sub.3 (CH.sub.2).sub.3 CH(CH.sub.3)-- ICH.sub.2                           CH.sub.2 CH.sub.2 --                                         CH.sub.3 (CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)-- CF.sub.3 CH.sub.2                              CH.sub.2 --                                                  CH.sub.3 CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.2 -- CF.sub.3 CF.sub.2                            CH.sub.2 --                                                ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                        CF.sub.3 CFHCF.sub.2 --                                                                         CF.sub.3 CH(CF.sub.3)--                                       FCH.sub.2 (CH.sub.2).sub.3 -- CH.sub.2 ═CH--                              BrCH.sub.2 (CH.sub.2).sub.3 -- CHCl═CH--                                  ClCH.sub.2 (CH.sub.2).sub.3 -- CCl.sub.2 ═CH--                            ICH.sub.2 (CH.sub.2).sub.3 -- CH.sub.2 ═CHCH.sub.2 --                     ClC(CH.sub.3).sub.2 CH.sub.2 -- CH.sub.2 ═CHCH.sub.2 CH.sub.2 --                           FCH.sub.2 (CH.sub.2).sub.4 -- (CH.sub.3).sub.2                               C═CH(CH.sub.2).sub.2 (CH.sub.3)C                          BrCH.sub.2 (CH.sub.2).sub.4 -- ═CHCH.sub.2 --                             ClCH.sub.2 (CH.sub.2).sub.4 -- (CH.sub.2 ═CH)(CH.sub.3 CH.sub.2                           CH.sub.2)CH--                                                 ICH.sub.2 (CH.sub.2).sub.4 -- (CH.sub.2 ═CHCH.sub.2).sub.2 CH--                            CH.sub.3 CHClCH.sub.2 -- CH.sub.2 ═C(CH.sub.3)CH.su                      b.2 --                                                        CH.sub.3 CH(CH.sub.2 Br)CH.sub.2 -- (CH.sub.3).sub.2 C═CHCH.sub.2                         --                                                            CH.sub.2 ClC(CH.sub.3).sub.2 CH.sub.2 -- CH═C(CH.sub.3)CH.sub.2                           CH.sub.2 --                                                   CH.sub.2 BrC(CH.sub.3).sub.2 CH.sub.2 -- (CH.sub.2 ═CH)(CH.sub.3                          CH.sub.2)CH--                                                 CH.sub.2 BrCHBrCH.sub.2 -- ClCH═CHCH.sub.2 --                             CCl.sub.3 CH.sub.2 -- CH.sub.3 CH═CHCH.sub.2 --                           CBr.sub.3 CH.sub.2 -- BrCH═CHCH.sub.2 --                                  CF.sub.2 HCF.sub.2 CH.sub.2 -- CH.sub.2 ═CClCH.sub.2 --                   CF.sub.3 CFHCF.sub.2 CH.sub.2 -- CH.sub.2 ═CBrCH.sub.2 --                 CF.sub.2 H(CF.sub.2).sub.3 CH.sub.2 -- CH.sub.2 ═C(CH.sub.2                               Cl)CH.sub.2 --                                                CH.sub.2 ClCH(CH.sub.3)-- ClCH.sub.2 CH═CHCH.sub.2 --                     CH.sub.2 BrCH(CH.sub.3)-- CH.sub.3 CH.sub.2 CH═CHCH.sub.2 CH.sub.2                        --                                                            CH.sub.2 FCH(CH.sub.2 F)-- ClCH.sub.2 CH═CHCH.sub.2 --                    CH.sub.2 ClCH(CH.sub.2 Cl)-- (Cl.sub.2)C═CHCH.sub.2 --                    CH.sub.2 BrCH(CH.sub.2 Br)-- (Br.sub.2)C═CHCH.sub.2 --                    CH.sub.2 BrCH.sub.2 CH(CH.sub.2 Br)-- (F.sub.2)C═CHCH.sub.2             ______________________________________                                                          --                                                      

                  TABLE 3                                                         ______________________________________                                        (CF.sub.3)(Cl)C═CHCH.sub.2 --                                                               CH.sub.2 ═CHCH(CH.sub.3 CH.sub.2 CH.sub.2)--                               (F)(CF.sub.2 Br)C═CHCH.sub.2 -- (CH.sub.3).sub.2                         ═CH(CH.sub.2).sub.2 CH(CH.sub.3)--                        (CF.sub.3)(F)C═CHCH.sub.2 -- CH.sub.3 (CH.sub.2).sub.3 CH.sub.2                           CH(CH═CH.sub.2)--                                         (Cl).sub.2 C═CHCH.sub.2 CH.sub.2 -- (CH.sub.3).sub.2 C═CH(CH.sub                      .2).sub.2                                                     (Br).sub.2 C═CHCH.sub.2 CH.sub.2 -- --CH(CH.sub.3)CH.sub.2 CH.sub.2                       --                                                            CH.sub.2 ═C(CH(CH.sub.3).sub.2)CH.sub.2 -- (CH.sub.3)(Cl)C═CHCH.                      sub.2 --                                                      CH.sub.3 CH═C(C.sub.2 H.sub.5)CH.sub.2 -- (Cl).sub.2 C═CH(CH.sub                      .2).sub.3 CH.sub.2 --                                         CH.sub.2 ═C (C.sub.2 H.sub.5)CH.sub.2 -- CH.tbd.CCH(CH.sub.3)--                            C.sub.2 H.sub.5 CH═C(CH.sub.3)CH.sub.2 -- CH.sub.3                       C.tbd.CCH.sub.2 --                                            C.sub.2 H.sub.5 CH═CHCH.sub.2 -- HC.tbd.CCH.sub.2 --                      CH.sub.3 CH═C(CH.sub.3)CH.sub.2 -- HC.tbd.CCH.sub.2 CH.sub.2 --                            CH.sub.3 (CH.sub.2).sub.3 CH═CHCH.sub.2 --                               CH.sub.3 CH.sub.2 CH.sub.2 C.tbd.CCH.sub.2 --                 CH.sub.2 ═CHCH(CH.sub.3)-- CH.sub.3 CH.sub.2 C.tbd.CCH.sub.2                              CH.sub.2 --                                                   CH.sub.3 CH═CHCH(CH.sub.3)-- HC.tbd.CCH(CH.sub.3)CH.sub.2 --                               CH.sub.3 CH═CHCH(C.sub.2 H.sub.5)-- HC.tbd.CCH(CH.s                      ub.3 (CH.sub.2).sub.4)--                                      CH.sub.2 ═CHCH.sub.2 CH.sub.2 CH(CH.sub.3)-- HC.tbd.CCH.sub.2                             CH(CH.sub.3)--                                                (CH.sub.3).sub.2 C═CHCH(CH.sub.3)-- CH.sub.3 CH.sub.2 C.tbd.CCH.sub.                      2 --                                                          CF.sub.3 CH═CHCH.sub.2 -- HC.tbd.CCH.sub.2 CH.sub.2 CH.sub.2 --                            CH.sub.2 ═CHCH(CH.sub.3)CH.sub.2 -- CH.sub.3                             C.tbd.CCH.sub.2 CH.sub.2 --                                   CH.sub.2 ═CHCH.sub.2 CH.sub.2 CH.sub.2 -- HC.tbd.CCH(C.sub.2                              H.sub.5)--                                                    CH.sub.2 ═CHCH.sub.2 (CH.sub.3)CH-- HC.tbd.CCH.sub.2 CH.sub.2                             CH.sub.2 CH.sub.2 --                                          CH.sub.2 ═CHCH(C.sub.2 H.sub.5)-- CH.sub.3 (CH.sub.2).sub.4 C                             .tbd.CCH.sub.2 CH.sub.2 --                                    CH.sub.3 (CH.sub.2).sub.2 CH═CHCH.sub.2 --                                CH.sub.3 CH═CH(CH.sub.2).sub.2 CH.sub.2 -- ClC.tbd.CCH(CH.sub.3)--                         CH.sub.2 ═CH(CH.sub.2).sub.3 CH.sub.2 -- BrC.tbd.CC                      H(CH.sub.3)--                                               ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                        ClC.tbd.CCH.sub.2 --                                                                             CH.sub.2 (CH.sub.3 O)CH.sub.2 CH.sub.2 --                    BrC.tbd.CCH.sub.2 -- CH.sub.3 CH(CH.sub.3 O)CH.sub.2 --                       ClC.tbd.CCH.sub.2 CH.sub.2 -- CH.sub.3 CH.sub.2 CH(CH.sub.3 O)--                                BrC.tbd.CCH.sub.2 CH.sub.2 -- CH.sub.3 OCH.sub.2                             CH(CH.sub.3)--                                               ClC.tbd.CCH(CH.sub.3)CH.sub.2 -- CH.sub.3 (CH.sub.2).sub.2 OCH.sub.2                           CH.sub.2 --                                                  BrC.tbd.CCH(CH.sub.3)CH.sub.2  CH.sub.3 CH.sub.2 OCH(CH.sub.3)CH.sub.2                         --                                                           ClC.tbd.CCH.sub.2 CH(CH.sub.3)-- CH.sub.3 CH.sub.2 OCH.sub.2 CH(CH.sub.3                       )--                                                          BrC.tbd.CCH.sub.2 CH(CH.sub.3)-- CH.sub.3 OCH(C.sub.2 H.sub.5)CH.sub.2                         --                                                           ClC.tbd.CCH.sub.2 CH.sub.2 CH.sub.2 -- CH.sub.3 OCH.sub.2 CH(C.sub.2                           H.sub.5)                                                     BrC.tbd.CCH.sub.2 CH.sub.2 CH.sub.2 -- C.sub.2 H.sub.5 CCH.sub.2                               CH.sub.2 CH.sub.2 --                                         ClC.tbd.CCH(C.sub.2 H.sub.5)-- CH.sub.3 OCH(CH.sub.3)CH.sub.2 CH.sub.2                         --                                                           BrC.tbd.CCH(C.sub.2 H.sub.5)-- CH.sub.3 OCH.sub.2 CH(CH.sub.3)CH.sub.2                         --                                                           CH.sub.3 (CH.sub.2).sub.3 OCH.sub.2 CH(CH.sub.3)-- CH.sub.3 OCH.sub.2                          CH.sub.2 CH(CH.sub.3)--                                      CH.sub.3 (CH.sub.2).sub.3 OCH.sub.2 CH.sub.2 -- CH.sub.3 SCH.sub.2                             (CH.sub.2).sub.2 CH.sub.2                                    (CH.sub.3).sub.2 CHOCH.sub.2 CH.sub.2 -- CH.sub.3 SCH.sub.2 --                (CH.sub.3).sub.2 (CH.sub.3 O)CCH.sub.2 CH.sub.2 -- CH.sub.3 CH.sub.2                           SCH.sub.2 --                                                 CH.sub.3 (CH.sub.3 O)CHCH.sub.2 CH.sub.2 -- CH.sub.3 CH.sub.2 CH.sub.2                         SCH.sub.2 --                                                 CH.sub.3 OCH.sub.2 CH.sub.2 -- (CH.sub.3).sub.2 CHSCH.sub.2 --                CH.sub.3 CH.sub.2 OCH.sub.2 -- CH.sub.3 SCH.sub.2 CH.sub.2 --                 CH.sub.3 OCH.sub.2 -- CH.sub.3 SCH(CH.sub.3)--                                (CH.sub.3).sub.2 CHOCH.sub.2 -- CH.sub.3 CH.sub.2 SCH.sub.2 CH.sub.2 --       CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.2 -- CH.sub.3 CH.sub.2 SCH(CH.sub.3)-                       -                                                            CH.sub.3 CH(OCH.sub.3)-- CH.sub.3 SCH.sub.2 CH.sub.2 CH.sub.2 --                                CH.sub.3 CH.sub.2 OCH.sub.2 CH.sub.2 -- CH.sub.3                             S(CH.sub.3)CHCH.sub.2 --                                     CH.sub.3 CH(OC.sub.2 H.sub.5)-- CH.sub.3 SCH(CH.sub.3 CH.sub.2)--           ______________________________________                                    

                  TABLE 5                                                         ______________________________________                                        CH.sub.3 SCH.sub.2 CH(CH.sub.3)--                                                                 3-sec-butyloxycyclohexyl                                    (CH.sub.3).sub.2 CHSCH.sub.2 CH.sub.2 --                                      CH.sub.3 CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 -- 3-tert-butyloxycyclohex                        yl                                                          CH.sub.3 SCH(CH.sub.3)C(CH.sub.3)H--                                          CH.sub.3 SCH(C.sub.2 H.sub.5)CH.sub.2 -- 4-methoxycyclohexyl                  CH.sub.3 SCH.sub.2 CH(C.sub.2 H.sub.5)-- 4-ethoxycyclohexyl                   CH.sub.3 CH.sub.2 SCH(CH.sub.3)CH.sub.2 -- 4-propoxycyclohexyl                CH.sub.3 CH.sub.2 SCH.sub.2 CH(CH.sub.3)-- 4-isopropoxycyclohexyl                                CH.sub.3 CH.sub.2 SCH.sub.2 CH.sub.2 CH.sub.2 --                             4-butoxycyclohexyl                                          CH.sub.3 SCH(CH.sub.3)CH.sub.2 CH.sub.2 -- 4-isobutyloxycyclohexyl                               CH.sub.3 SCH.sub.2 CH(CH.sub.3)CH.sub.2 -- 4-sec-buty                        loxycyclohexyl                                              CH.sub.3 SCH.sub.2 CH.sub.2 CH(CH.sub.3)-- 4-tert-butyloxycyclohexyl                             (CH.sub.3).sub.3 CSCH.sub.2 CH.sub.2 --                    (CH.sub.3).sub.2 CHCH.sub.2 SCH.sub.2 CH.sub.2 -- 2-methoxycyclopentyl                           CH.sub.3 CH.sub.2 CH(CH.sub.3)SCH.sub.2 CH.sub.2 --                          2-ethoxycyclopentyl                                         (CH.sub.3).sub.3 CSCH.sub.2 CH.sub.2 CH.sub.2 -- 2-propoxycyclopentyl                            (CH.sub.3).sub.2 CHCH.sub.2 SCH.sub.2 CH.sub.2                               CH.sub.2 -- 2-isopropoxycyclopentyl                         CH.sub.3 CH.sub.2 CH(CH.sub.3)SCH.sub.2 CH.sub.2 CH.sub.2 -- 2-butoxycyc                        lopentyl                                                    3-methoxycyclohexyl 2-isobutyloxycyclopentyl                                  3-ethoxycyclohexyl 2-sec-butyloxycyclopentyl                                  3-propoxycyclohexyl 2-tert-butyloxycyclopentyl                                3-isopropoxycyclohexyl                                                        3-butoxycyclohexyl cyclopropyl                                                3-isobutyloxycyclohexyl cyclobutyl                                             cyclopentyl                                                                ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                        cyclohexyl        3-(difluorobromomethoxy)-                                      cyclohexyl                                                                   2,3-dimethylcyclohexyl                                                         4-(difluorobromomethoxy)-                                                    2-ethylcyclohexyl cyclohexyl                                                  3,3,5,5-tetramethyl- 3-(difluorobromomethoxy)-                                cyclohexyl cyclopentyl                                                        3,4-dimethylcyclohexyl 3-(2,2,2-trifluoroethoxy)-                              cyclohexyl                                                                   3,5-dimethylcyclohexyl                                                         4-(2,2,2-trifluoroethoxy)-                                                   4-ethylcyclohexyl cyclohexyl                                                  2-methylcyclohexyl 3-(2,2,2-trifluoroethoxy)-                                  cyclopentyl                                                                  3-methylcyclohexyl                                                             3-(1,1,2,2,2-pentafluoro-                                                    4-methylcyclohexyl ethoxy)cyclohexyl                                          3-methylcyclopentyl 4-(1,1,2,2,2-pentafluro-                                   ethoxy)cyclohexyl                                                            2-methylcyclopentyl                                                            3-(1,1,2,2,2-pentafluoro-                                                    3-(trifluoromethoxy)- ethoxy)cyclopentyl                                      cyclohexyl                                                                     3-(2-chloroethoxy)-                                                          4-(trifluoromethoxy)- cyclohexyl                                              cyclohexyl                                                                     3-(2-chloroethoxy)-                                                          3-(trifluoromethoxy) cyclopentyl                                              cyclopentyl                                                                    4-(2-chloroethoxy)-                                                          3-(difluoromethoxy) cyclohexyl                                                cyclohexyl                                                                     3-(2-bromoethoxy)-                                                           4-(difluoromethoxy)- cyclohexyl                                               cyclohexyl                                                                    3-(difluoromethoxy)-                                                          cyclopentyl                                                                 ______________________________________                                    

                                      TABLE 7                                     __________________________________________________________________________              3-(2-bromoethoxy)-   3-(1,2,2,3,3,3-hexa-                             cyclopentyl fluoropropoxy)cyclopentyl                                         4-(2-bromoethoxy)- 4-(1,2,2,3,3,3-hexa-                                       cyclohexyl fluoropropoxy)cyclohexyl                                           3-(2-chloro-1,1,2-tri- 2-cyclohexylethyl                                      fluoroethoxy)cyclohexyl cyclobutylmethyl                                      3-(2-chloro-1,1,2-tri- cyclopropylmethyl                                      fluoroethoxy)cyclopentyl                                                      4-(2-chloro-1,1,2-tri- 1-cyclopropylethyl                                     fluoroethoxy)cyclohexyl cyclohexylmethyl                                      3-(2-bromo-1,1,2-tri- cyclopentylmethyl                                       fluoroethoxy)cyclohexyl                                                       3-(2-bromo-1,1,2-tri- 2-methylcyclopropane-                                   fluoroethoxy)cyclopentyl methyl                                               4-(2-bromo-1,1,2-tri- 3-cyclopentylpropyl                                     fluoroethoxy)cyclohexyl 3-cyclohexylpropyl                                    3-(1,1,2,2-tetrafluoro- 2-(2-methylcycropropyl-                               ethoxy)cyclohexyl ethyl                                                       3-(1,1,2,2-tetrafluoro- 2-cyclohexenyl                                        ethoxy)cyclopentyl                                                            4-(1,1,2,2-tetrafluoro- 3,5,5-trimethyl-2-                                    ethoxy)cyclohexyl cyclohexenyl                                                3-(1,2,2,3,3,3-hexa- 3-methyl-2-cyclohexenyl                                  fluoropropoxy)cyclohexyl 2-(3-cyclohexenyl)ethyl                               (3-cyclohexenyl)methyl                                                        (1-cyclopentenyl)methyl                                                       2-cyclopentenyl                                                               3-cyclopentenyl                                                               3-cyclohexenyl                                                             __________________________________________________________________________                                      #STR18##                                                                      #STR19##                                                                      #STR20##                                       -                                                                                                            #STR21##                                                                      #STR22##                                       -                                                                                                            #STR23##                                                                      #STR24##                                       -                                                                                                            #STR25##                                                                      #STR26##                                       -                                                                                                            #STR27##                                                                      #STR28##                                       -                                                                                                            #STR29##                                                                      #STR30##                                       -                                                                                                            #STR31##                                                                      #STR32##                                       -                                                                                                            #STR33##                                                                      #STR34##                                       -                                                                                                            #STR35##                                                                      #STR36##                                                                      #STR37##                                       -                                                                                                            #STR38##                                                                      #STR39##                                       -                                                                                                            #STR40##                                                                      #STR41##                                       -                                                                                                            #STR42##                                                                      #STR43##                                       -                                                                                                            #STR44##                                                                      #STR45##                                       -                                                                                                            #STR46##                                                                     ##STR47##                                    __________________________________________________________________________

(in which (R₁₂)_(l) is as defined in Tables 8 to 21).

                  TABLE 8                                                         ______________________________________                                        (R.sub.12).sub.l  (R.sub.12).sub.l                                            ______________________________________                                        H                 3-OCH.sub.2 C.sub.6 H.sub.5                                   2-CH.sub.3 3-OCF.sub.3                                                        2-F 3-OCF.sub.2 CF.sub.2 H                                                    2-CF.sub.3 3-NO.sub.2                                                         2-Cl 3-OC.sub.6 H.sub.4 (p--CH.sub.3)                                         2-Br 3-OC.sub.6 H.sub.4 (p--C(CH.sub.3).sub.3)                                2-I 3-OC.sub.6 H.sub.4 (m--CF.sub.3)                                          2-OCH.sub.3 3-OC.sub.6 H.sub.4 (p--Cl)                                        2-OCH.sub.2 CH.sub.3 3-OC.sub.6 H.sub.3(3,4--Cl.sub.2)                        2-C.sub.5 H.sub.5 3-OC.sub.6 H.sub.3 (3,5--Cl.sub.2)                          2-NO.sub.2 3-OC.sub.6 H.sub.4 (p--OCH.sub.3)                                  2-C.sub.6 H.sub.4 (p--CF.sub.3) 3-CN                                          2-CH.sub.2 C.sub.6 H.sub.5 3-CH.sub.3                                         2-OC.sub.6 H.sub.5 3-CH.sub.2 CH.sub.3                                        2-CN 3-CH.sub.2 CH.sub.2 CH.sub.3                                             3-CH.sub.3 3-CH(CH.sub.3).sub.2                                               3-F 3-C(CH.sub.3).sub.3                                                       3-CF.sub.3 3-OCF.sub.2 Br                                                     3-Cl 3-OCF.sub.2 H                                                            3-Br 3-OCF.sub.2 CFHCF.sub.3                                                  3-I 3-OCH.sub.2 CF.sub.2                                                      3-OCH.sub.3 3-OCH.sub.2 CH.sub.3                                              3-OC.sub.6 H.sub.5 3-OCH.sub.2 CH.sub.2 CH.sub.3                            ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                        3-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                            3-(3-cyclopentenyl)                                          3-OCH(CH.sub.3).sub.2 3-(4-cyclopentenyl)                                     3-OCH(CH.sub.3)CH.sub.2 CH.sub.3 3-C--OCH.sub.3                               3-OCH.sub.2 CH(CH.sub.3)CH.sub.3 ∥                                   3-OC(CH.sub.3).sub.3 O                                                        3-OCH.sub.2 CH═CH.sub.2 3-C--OCH.sub.2 CH.sub.3                           3-OCH.sub.2 CH═C(Cl).sub.2 ∥                                     3-OCH.sub.2 CH═C(Br).sub.2 O                                              3-OCH.sub.2 CH═CH(Cl) 3-C--OCH.sub.2 CH.sub.2 CH.sub.3                    3-OCH.sub.2 C(Cl)═CH(Cl) ∥                                       3-OCH.sub.2 CH═(CH.sub.3).sub.2 O                                         3-OCH.sub.2 CH═CH(CH.sub.3) 3-C--OCH(CH.sub.3).sub.2                      3-OCH.sub.2 C(CH.sub.3)═CH.sub.2 ∥                               3-OCH.sub.2 CBr═CH(Br) O                                                  3-CH.sub.2 OH 3-C--OC(CH.sub.3).sub.3                                         3-CH.sub.2 OCH.sub.3 ∥                                               3-CH.sub.2 OCH.sub.2 CH.sub.3 O                                               3-CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.3 3-cyclopropyloxy                       3-CH.sub.2 OCH(CH.sub.3).sub.2 3-cyclobutyloxy                                3-OCH.sub.2 C.tbd.CH 3-cyclopentyloxy                                         3-OCH.sub.2 C.tbd.C--Cl 3-cyclohexyloxy                                       3-OCH.sub.2 C.tbd.C--Br 3-(3-cyclohexenyl)                                    3-OCH.sub.2 C.tbd.C--CH.sub.3 3-(4-cyclohexenyl)                              3-OCH(CH.sub.3)C.tbd.CH 3-(5-cyclohexenyl)                                    3-cyclopentyl 3-(3-cyclopentenyloxy)                                          3-cyclohexyl 3-(4-cyclopentenyloxy)                                         ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                        3-(3-cyclohexenyloxy)                                                                            3-OCH.sub.2 C.sub.6 H.sub.4 (p--CH.sub.3)                    3-(4-cyclohexenyloxy) 3-OCH.sub.2 C.sub.6 H.sub.4 (p--CF.sub.3)                                 3-(5-cyclohexenyloxy) 3-SCF.sub.2 CF.sub.2 H                3-CH.sub.2 C.sub.6 H.sub.5 3-SCH.sub.3                                        3-OCH.sub.2 CH═C(Cl)(CH.sub.3) 3-SCH.sub.2 CH.sub.3                       3-OCH.sub.2 CH═C(CH.sub.3)(CF.sub.3) 3-OCH.sub.2 C(Cl).tbd.CH.sub.2       3-OC.sub.6 H.sub.4 (o--Cl) 4-CH.sub.3                                         3-OC.sub.6 H.sub.4 (o--F) 4-CH.sub.2 CH.sub.3                                 3-OC.sub.6 H.sub.4 (o--CH.sub.3) 4-CH(CH.sub.3).sub.2                         3-OC.sub.6 H.sub.4 (m--Cl) 4-C(CH.sub.3).sub.3                                3-OC.sub.6 H.sub.4 (m--F) 4-CH.sub.2 (CH.sub.2).sub.2 CH.sub.3                3-OC.sub.6 H.sub.4 (m--CH.sub.3) 4-F                                          3-OCH.sub.2 C.sub.6 H.sub.4 (o--Cl) 4-CF.sub.3                                3-OCH.sub.2 C.sub.6 H.sub.4 (o--F) 4-Cl                                       3-OCH.sub.2 C.sub.6 H.sub.4 (o--Br) 4-Br                                      3-OCH.sub.2 C.sub.6 H.sub.4 (o--CH.sub.3) 4-OCH.sub.3                         3-OCH.sub.2 C.sub.6 H.sub.4 (o--CF.sub.3) 4-OCH.sub.2 CH.sub.3                3-OCH.sub.2 C.sub.6 H.sub.4 (m--Cl) 4-OCH.sub.2 (CH.sub.2).sub.2                               CH.sub.3                                                     3-OCH.sub.2 C.sub.6 H.sub.4 (m--F) 4-OCF.sub.3                                3-OCH.sub.2 C.sub.6 H.sub.4 (m--Br) 4-C.sub.6 H.sub.5                         3-OCH.sub.2 C.sub.6 H.sub.4 (m--CH.sub.3) 4-OCH.sub.2 C.sub.6 H.sub.5                           3-OCH.sub.2 C.sub.6 H.sub.4 (m--CF.sub.3) 4-OCH.sub.2                        CH.sub.2 CH.sub.3                                            3-OCH.sub.2 C.sub.6 H.sub.4 (p--Cl) 4-OCF.sub.3                               3-OCH.sub.2 C.sub.6 H.sub.4 (p--Br) 4-SCH.sub.3                               3-OCH.sub.2 C.sub.6 H.sub.4 (p--F) 4-NO.sub.2                               ______________________________________                                    

                  TABLE 11                                                        ______________________________________                                        4-OC.sub.6 H.sub.5                                                                              4-OCH.sub.2 CH═CH(Cl)                                     4-CH.sub.2 (CH.sub.2).sub.3 CH.sub.3 4-OCH.sub.2 C(Cl)═CH(Cl)                              4-CH.sub.2 (CH.sub.2).sub.4 CH.sub.3 4-OCH.sub.2                             CH═C(CH.sub.3).sub.2                                      4-CH.sub.2 (CH.sub.2).sub.5 CH.sub.3 4-OCH.sub.2 CH═CH(CH.sub.3)                           4-CH.sub.2 (CH.sub.2).sub.6 CH.sub.3 4-OCH.sub.2                             C(CH.sub.3)═CH.sub.2                                      4-CH═CH.sub.2 4-OCH.sub.2 C(Cl)═CH.sub.2                              4-I 4-OCH.sub.2 C(Br)═CH.sub.2 (Br)                                       4-OCH.sub.2 (CH.sub.2).sub.3 CH.sub.3 4-CH.sub.2 OH                           4-OCH.sub.2 (CH.sub.2).sub.4 CH.sub.3 4-CH.sub.2 OCH.sub.3                    4-OCH.sub.2 (CH.sub.2).sub.5 CH.sub.3 4-CH.sub.2 OCH.sub.2 CH.sub.3                            4-OCH(CH.sub.3).sub.2 4-CH.sub.2 OCH.sub.2 CH.sub.2                          CH.sub.3                                                      4-(2-cyclohexenyl) 4-CH.sub.2 OCH(CH.sub.3).sub.2                             4-SCH.sub.2 CH.sub.3 4-OCH.sub.2 C.tbd.CH                                     4-C.sub.6 H.sub.4 (p--CH.sub.2 CH.sub.3) 4-OCH.sub.2 C.tbd.C--Cl                               4-CN 4-OCH.sub.2 C.tbd.C--Br                                 4-OCF.sub.2 Br 4-OCH.sub.2 C.tbd.C--CH.sub.3                                  4-OCF.sub.2 H 4-OCH(CH.sub.3)C.tbd.CH                                         4-OCF.sub.2 CFHCF.sub.3 4-cyclopentyl                                         4-OCH.sub.2 CF.sub.3 4-cyclohexyl                                             4-OCF.sub.2 CF.sub.2 H 4-(3-cyclopentenyl)                                    4-SCF.sub.2 CF.sub.2 H 4-(4-cyclopentenyl)                                    4-SCH(CH.sub.3).sub.2 4-COCH.sub.3                                            4-OCH.sub.2 CH═CH.sub.2 ∥                                        4-OCH.sub.2 CH═C(Cl).sub.2 O                                              4-OCH.sub.2 CH═C(Br).sub.2                                              ______________________________________                                    

                  TABLE 12                                                        ______________________________________                                                             4-OCH8##                                                                    .sub.2 CH=C(Cl)CH.sub.3  4-OCH.sub.2 CH=C(CH.sub.3)CF.s                       ub.3  4-OC.sub.6 H.sub.4 (o-Cl)                               -                                                                                               4-OC.sub.6 H.sub.4 (o-F)  4-OC.sub.6 H.sub.4                                (o-CH.sub.3)  4-OC.sub.6 H.sub.4 (m-Cl)                       -                                                                                               4-OC.sub.6 H.sub.4 (m-F)  4-OC.sub.6 H.sub.4                                (m-CH.sub.3)  4-OCH.sub.2 C.sub.6 H.sub.4 (o-Cl)                                -                                                                             4-OCH.sub.2 C.sub.6 H.sub.4 (o-F)  4-OCH.sub.2                              C.sub.6 H.sub.4 (o-Br)  4-OCH.sub.2 C.sub.6 H.sub.4                           (o-CH.sub.3)                                                  - 4-cyclopropyloxy 4-OCH.sub.2 C.sub.6 H.sub.4 (o-CF.sub.3)                  4-cyclobutyloxy 4-OCH.sub.2 C.sub.6 H.sub.4 (m-Cl)                            4-cyclopentyloxy 4-OCH.sub.2 C.sub.6 H.sub.4 (m-F)                            4-cyclohexyloxy 4-OCH.sub.2 C.sub.6 H.sub.4 (m-Br)                            4-(3-cyclohexenyl) 4-OCH.sub.2 C.sub.6 H.sub.4 (m-CH.sub.3)                   4-(4-cyclohexenyl) 4-OCH.sub.2 C.sub.6 H.sub.4 (m-CF.sub.3)                   4-(5-cyclohexenyl) 4-OCH.sub.2 C.sub.6 H.sub.4 (p-Cl)                         4-(3-cyclopentenyloxy) 4-OCH.sub.2 C.sub.6 H.sub.4 (p-Br)                     4-(4-cyclopentenyloxy) 4-OCH.sub.2 C.sub.6 H.sub.4 (p-F)                      4-(3-cyclohexenyloxy) 4-OCH.sub.2 C.sub.6 H.sub.4 (p-CH.sub.3)                4-(4-cyclohexenyloxy) 4-OCH.sub.2 C.sub.6 H.sub.4 (p-CF.sub.3)                4-(5-cyclohexenyloxy) 4-SCF.sub.2 CF.sub.2 H                                  4-CH.sub.2 C.sub.6 H.sub.5 4-OCH.sub.2 C(Cl)=CH.sub.2                       ______________________________________                                    

                  TABLE 13                                                        ______________________________________                                        2,6-F.sub.2        3-CH.sub.3, 4-NO.sub.2                                       2,3-F.sub.2 3-NO.sub.2, 4-CH.sub.3                                            2-F, 6-Cl 2-NO.sub.2, 4-Cl                                                    2,6-Cl.sub.2 3-NO.sub.2, 4-Cl                                                 2,3-(OCH.sub.3).sub.2 2-Cl, 5-NO.sub.2                                        2,4-(CH.sub.3).sub.2 2-NO.sub.2, 5-Cl                                         2,4-(CH.sub.3).sub.2 3-OCH.sub.3, 4-NO.sub.2                                  2,5-(CH.sub.3).sub.2 2-CH.sub.3, 3-F                                          3,4-F.sub.2 2-F, 3-CF.sub.3                                                   2,4-F.sub.2 2,3-Cl.sub.2                                                      2,5-F.sub.2 2,6-(OCH.sub.3).sub.2                                             2,4-Cl.sub.2 2-Cl, 6-NO.sub.2                                                 3,4-Cl.sub.2 2-NO.sub.2, 3-OCH.sub.3                                          2,5-Cl.sub.2 2,6-(NO.sub.2).sub.2                                             2,4-(OCH.sub.3).sub.2 2-Cl, 5-CF.sub.3                                        2,5-(OCH.sub.3).sub.2 3-Cl, 4-F                                               2-OCH.sub.3, 5-Br 2-Cl, 4-F                                                   3,4-OCH.sub.3 O-- 3-Br, 4-F                                                   3,5-(CH.sub.3).sub.2 2-OCH.sub.3, 5-Br                                        3,5-(CF.sub.3).sub.2 3,4-OCH.sub.2 CH.sub.2 O--                               3,5-F.sub.2 3-NO.sub.2, 5-Cl                                                  3,5-Cl.sub.2 2,4-(NO.sub.2).sub.2                                             3,5-(OCH.sub.3).sub.2 3,5-(OCH.sub.2 C.sub.6 H.sub.5).sub.2                   2-CH.sub.3, 4-C.sub.6 H.sub.5 3,4-(OCH.sub.2 C.sub.6 H.sub.5).sub.2                             2-NO.sub.2, 4-Cl 2-F, 6-CF.sub.3                            2-NO.sub.2, 5-CH.sub.3 2-F, 3-CF.sub.3                                      ______________________________________                                    

                  TABLE 14                                                        ______________________________________                                        2,6-(CF.sub.3).sub.2                                                                             2-CH.sub.3, 5-NO.sub.2                                       2-NO.sub.2, 6-CH.sub.3 2-NO.sub.2, 4-CF.sub.3                                 2-NO.sub.2, 3-CH.sub.3 2-F, 5-NO.sub.2                                        2-CH.sub.3, 3-NO.sub.2 2-Cl, 4-NO.sub.2                                       2-NO.sub.2, 3-Cl 3-NO.sub.2, 4-F                                              2-Cl, 3-NO.sub.2 2-Br, 5-NO.sub.2                                             2-Br, 3-NO.sub.2 3-NO.sub.2, 4-OCH.sub.3                                      2-NO.sub.2, 3-OCH.sub.3 3,5-(C(CH.sub.3).sub.3).sub.2                         2-CH.sub.3, 5-F 2,3-(CH.sub.3).sub.2, 4-OCH.sub.3                             3-F, 4-CH.sub.3 3-CH.sub.3, 2,4-(OCH.sub.3).sub.2                             3-Br, 4-CH.sub.3 2,3,4-(OCH.sub.3).sub.3                                      2,4-(CF.sub.3).sub.2 3,4,5-(OCH.sub.3).sub.3                                  3-I, 4-CH.sub.3 2,3,4,5,6-F.sub.5                                             2-Cl, 5-CF.sub.3 2,4,6-(CH.sub.3).sub.3                                       2,5-(CF.sub.3).sub.2 2,3,6-Cl.sub.3                                           2-F, 4-CF.sub.3 3,4-(OCH.sub.3).sub.2, 5-Br                                   2-Cl, 4-F 2,4,6-(OCH.sub.3).sub.3                                             3-OCH.sub.3, 4-CH.sub.3 2,4-(OCH.sub.3).sub.2, 5-Br                           2-OCH.sub.3, 4-Cl 2-Br, 4,5-(OCH.sub.3).sub.2                                 2-OCH.sub.3, 5-Cl 2,4,5-(OCH.sub.3).sub.3                                     2-Br, 5-OCH.sub.3 2-NO.sub.2, 3,4-(OCH.sub.3).sub.2                           3,4-(OCH.sub.2 CH.sub.3).sub.2 2-NO.sub.2, 3,4-OCH.sub.2 O--                  2-Cl, 5-SCH.sub.3 2,5-Cl.sub.2, 4-CHF.sub.2                                   2-OCH.sub.3, 4-SCH.sub.3 2,3,4-F.sub.3                                        3-CH.sub.3, 4-NO.sub.2 2,3,6-Cl.sub.3                                       ______________________________________                                    

                  TABLE 15                                                        ______________________________________                                        2,3,5,6-F.sub.4    3-Cl, 4-OCH.sub.2 CF.sub.3                                   2,3,6-F.sub.3 3-Cl, 4-OC.sub.6 H.sub.5                                        2,4,6-F.sub.3 3-Cl, 4-OCH.sub.2 C.sub.6 H.sub.5                               3,4,5-F.sub.3 3-Cl, 4-cyclopentyloxy                                          2,4,6-Cl.sub.3 3-Cl, 4-cyclohexyloxy                                          2,3,5-Cl.sub.3 3-Br, 4 -OCH.sub.3                                             2,3,5-I.sub.3 3-Br, 4-OCH.sub.2 CH.sub.3                                      2,4,5-F.sub.3 3-Br, 4-OCH.sub.2 CH.sub.2 CH.sub.3                             2,4-Cl.sub.2, 5-F 3-Br, 4-OCH(CH.sub.3).sub.2                                 2,3,4,5-F.sub.4 3-Br, 4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3                   2,3,5,6-F.sub.4, 4-CH.sub.3 3-Br, 4-OCH(CH.sub.3)CH.sub.2 CH.sub.3                              2,3,5,6-F.sub.4, 4-Br 3-Br, 4-OCH.sub.2 CH(CH.sub.3).s                       ub.2                                                         3-Cl, 4-OCH.sub.3 3-Br, 4-OC(CH.sub.3).sub.3                                  3-Cl, 4-OCH.sub.2 CH.sub.3 3-Br, 4-OCF.sub.3                                  3-Cl, 4-OCH.sub.2 CH.sub.2 CH.sub.3 3-Br, 4-OCF.sub.2 Br                      3-Cl, 4-OCH(CH.sub.3).sub.2 3-Br, 4-OCF.sub.2 H                               3-Cl, 4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3 3-Br, 4-OCF.sub.2 CF.sub.2                         H                                                            3-Cl, 4-OCH(CH.sub.3)CH.sub.2 CH.sub.3 3-Br, 4-OCF.sub.2 CFHCF.sub.3                            3-Cl, 4-OCH.sub.2 CH(CH.sub.3).sub.2 3-Br, 4-OCH.sub.2                        CF.sub.3                                                    3-Cl, 4-OC(CH.sub.3).sub.3 3-Br, 4-OC.sub.6 H.sub.5                           3-Cl, 4-OCF.sub.3 3-Br, 4-OCH.sub.2 C.sub.6 H.sub.5                           3-Cl, 4-OCF.sub.2 Br 3-Br, 4-cyclopentyloxy                                   3-Cl, 4-OCF.sub.2 H 3-Br, 4-cyclohexyloxy                                     3-Cl, 4-OCF.sub.2 CF.sub.2 H 3-F, 4-OCH.sub.3                                 3-Cl, 4-OCF.sub.2 CFHCF.sub.3 3-F, 4-OCH.sub.2 CH.sub.3                     ______________________________________                                    

                  TABLE 16                                                        ______________________________________                                        3-F, 4-OCH.sub.2 CH.sub.2 CH.sub.3                                                              3-CH.sub.3, 4-OCF.sub.3                                       3-F, 4-OCH(CH.sub.3).sub.2 3-CH.sub.3, 4-OCF.sub.2 Br                         3-F, 4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3 3-CH.sub.3, 4-OCF.sub.2 H                           3-F, 4-OCH(CH.sub.3)CH.sub.2 CH.sub.3 3-CH.sub.3,                            4-OCF.sub.2 CF.sub.2 H                                        3-F, 4-OCH.sub.2 CH(CH.sub.3).sub.2 3-CH.sub.3, 4-OCF.sub.2 CFHCF.sub.3       3-F, 4-OC(CH.sub.3).sub.3 3-CH.sub.3, 4-OCH.sub.2 CF.sub.3                    3-F, 4-OCF.sub.3 3-CH.sub.3, 4-OC.sub.6 H.sub.5                               3-F, 4-OCF.sub.2 Br 3-CH.sub.3, 4-OCH.sub.2 C.sub.6 H.sub.5                   3-F, 4-OCF.sub.2 H 3-CH.sub.3, 4-cyclopentyloxy                               3-F, 4-OCF.sub.2 CF.sub.2 H 3-CH.sub.3, 4-cyclohexyloxy                       3-F, 4-OCF.sub.2 CFHCF.sub.3 3-OCH.sub.3, 4-OCH.sub.3                         3-F, 4-OCH.sub.2 CF.sub.3 3-OCH.sub.3, 4-OCH.sub.2 CH.sub.3                   3-F, 4-OC.sub.6 H.sub.5 3-OCH.sub.3, 4-OCH.sub.2 CH.sub.2 CH.sub.3                             3-F, 4-OCH.sub.2 C.sub.6 H.sub.5 3-OCH.sub.3, 4-OCH(CH.                      sub.3).sub.2                                                  3-F, 4-cyclopentyloxy 3-OCH.sub.3, 4-OCH.sub.2 (CH.sub.2).sub.2                               CH.sub.3                                                      3-F, 4-cyclohexyloxy 3-OCH.sub.3, 4-OCH(CH.sub.3)CH.sub.2 CH.sub.3                             3-CH.sub.3, 4-OCH.sub.3 3-OCH.sub.3, OCH.sub.2                               CH(CH.sub.3).sub.2                                            3-CH.sub.3, 4-OCH.sub.2 CH.sub.3 3-OCH.sub.3, 4-OC(CH.sub.3).sub.3                             3-CH.sub.3, 4-OCH.sub.2 CH.sub.2 CH.sub.3 3-OCH.sub.3,                       4-OCF.sub.3                                                   3-CH.sub.3, 4-OCH(CH.sub.3).sub.2 3-OCH.sub.3, 4-OCF.sub.2 Br                 3-CH.sub.3, 4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3 3-OCH.sub.3, 4-OCF.sub                      .2 H                                                          3-CH.sub.3, 4-OCH(CH.sub.3)CH.sub.2 CH.sub.3 3-OCH.sub.3, 4-OCF.sub.2                         CF.sub.2 H                                                    3-CH.sub.3, 4-OCH.sub.2 CH(CH.sub.3).sub.2 3-OCH.sub.3, 4-OCF.sub.2                           CFHCF.sub.3                                                   3-CH.sub.3, 4-OC(CH.sub.3).sub.3 3-OCH.sub.3, 4-OCH.sub.2 CF.sub.3          ______________________________________                                    

                  TABLE 17                                                        ______________________________________                                        3-OCH.sub.3, 4-OC.sub.6 H.sub.5                                                                   4-Cl, 3-OCH.sub.3                                           3-OCH.sub.3, 4-OCH.sub.2 C.sub.6 H.sub.5 4-Cl, 3-OCH.sub.2 CH.sub.3                              3-OCH.sub.3, 4-cyclopentyloxy 4-Cl, 3-OCH.sub.2                              CH.sub.2 CH.sub.3                                           3-OCH.sub.3, 4-cyclopentyloxy 4-Cl, 3-OCH(CH.sub.3).sub.2                     3-OCH.sub.2 CH.sub.3, 4-OCH.sub.3 4-Cl, 3-OCH.sub.2 (CH.sub.2).sub.2                            CH.sub.3                                                    3-OCH.sub.2 CH.sub.3, 4-OCH.sub.2 CH.sub.3 4-Cl, 3-OCH(CH.sub.3)CH.sub.2                         CH.sub.3                                                   3-OCH.sub.2 CH.sub.3, 4-OCH.sub.2 CH.sub.2 CH.sub.3 -- 4-Cl, 3-OCH.sub.2                         CH(CH.sub.3).sub.2                                         3-OCH.sub.2 CH.sub.3, 4-OCH(CH.sub.3).sub.2 4-Cl, 3-OC(CH.sub.3)                                 3-OCH.sub.2 CH.sub.3, 4-Cl, 3-OCF.sub.3                    4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3 4-Cl, 3-OCF.sub.2 Br                    3-OCH.sub.2 CH.sub.3, 4-Cl, 3-OCF.sub.2 H                                     4-OCH(CH.sub.3)CH.sub.2 CH.sub.3 4-Cl, 3-OCF.sub.2 CF.sub.2 H                 3-OCH.sub.2 CH.sub.3, 4-OCH.sub.2 CH(CH.sub.3).sub.2 4-Cl, 3-OCF.sub.2                          CFHCF.sub.3                                                 3-OCH.sub.2 CH.sub.3, 4-OC(CH.sub.3).sub.3 4-Cl, 3-OCH.sub.2 CF.sub.3                            3-OCH.sub.2 CH.sub.3, 4-OCF.sub.3 4-Cl, 3-OC.sub.6                           H.sub.5                                                     3-OCH.sub.2 CH.sub.3, 4-OCF.sub.2 Br 4-Cl, 3-OCH.sub.2 C.sub.6 H.sub.5                           3-OCH.sub.2 CH.sub.3, 4-OCF.sub.2 H 4-Cl, 3-cyclopent                        yloxy                                                       3-OCH.sub.2 CH.sub.3, 4-OCF.sub.2 CF.sub.2 H 4-Cl, 3-cyclohexyloxy                               3-OCH.sub.2 CH.sub.3, 4-OCF.sub.2 CFHCF.sub.3 4-Br,                          3-OCH.sub.3                                                 3-OCH.sub.2 CH.sub.3, 4-OCH.sub.2 CF.sub.3 4-Br, 3-OCH.sub.2 CH.sub.3                            3-OCH.sub.2 CH.sub.3, 4-OC.sub.6 H.sub.5 4-Br,                               3-OCH.sub.2 CH.sub.2 CH.sub.3                               3-OCH.sub.2 CH.sub.3, 4-OCH.sub.2 C.sub.6 H.sub.5 4-Br, 3-OCH(CH.sub.3).                        sub.2                                                       3-OCH.sub.2 CH.sub.3, 4-Br, 3-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3                                4-cyclohexyloxy 4-Br, 3-OCH(CH.sub.3)CH.sub.2                                CH.sub.3                                                    3-OCH.sub.2 CH.sub.3, 4-Br, 3-OCH.sub.2 CH(CH.sub.3).sub.2                    4-cyclopentyloxy 4-Br, 3-OC(CH.sub.3).sub.3                                 ______________________________________                                    

                  TABLE 18                                                        ______________________________________                                        4-Br, 3-OCF.sub.3 4-F, 4-OCH.sub.2 C.sub.6 H.sub.5                              4-Br, 3-OCF.sub.2 Br 4-F, 3-cyclopentyloxy                                    4-Br, 3-OCF.sub.2 H 4-F, 3-cyclohexyloxy                                      4-Br, 3-OCF.sub.2 CF.sub.2 H 4-CH.sub.3, 3-OCH.sub.3                          4-Br, 3-OCF.sub.2 CFHCF.sub.3 4-CH.sub.3, 3-OCH.sub.2 CH.sub.3                4-Br, 3-OCH.sub.2 CF.sub.3 4-CH.sub.3, 3-OCH.sub.2 CH.sub.2 CH.sub.3                           4-Br, 3-OC.sub.6 H.sub.5 4-CH.sub.3, 3-OCH(CH.sub.3).su                      b.2                                                           4-Br, 3-OCH.sub.2 C.sub.6 H.sub.5 4-CH.sub.3, 3-OCH.sub.2 (CH.sub.2).sub                      .2 CH.sub.3                                                   4-Br, 3-cyclopentyloxy 4-CH.sub.3, 3-OCH(CH.sub.3)CH.sub.2 CH.sub.3                            4-Br, 3-cyclohexyloxy 4-CH.sub.3, 3-OCH.sub.2 CH(CH.sub                      .3).sub.2                                                     4-F, 3-OCH.sub.3 4-CH.sub.3, 3-OC(CH.sub.3).sub.3                             4-F, 3-OCH.sub.2 CH.sub.3 4-CH.sub.3, 3-OCF.sub.3                             4-F, 3-OCH.sub.2 CH.sub.2 CH.sub.3 4-CH.sub.3, 3-OCF.sub.2 Br                 4-F, 3-OCH(CH.sub.3).sub.2 4-CH.sub.3, 3-OCF.sub.2 H                          4-F, 3-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3 4-CH.sub.3, 3-OCF.sub.2                            CF.sub.2 H                                                    4-F, 3-OCH(CH.sub.3)CH.sub.2 CH.sub.3 4-CH.sub.3, 3-OCF.sub.2 CFHCF.sub.                      3                                                             4-F, 3-OCH.sub.2 CH(CH.sub.3).sub.2 4-CH.sub.3, 3-OCH.sub.2 CF.sub.3                           4-F, 3-OC(CH.sub.3).sub.3 4-CH.sub.3, 3-OC.sub.6                             H.sub.5                                                       4-F, 3-OCF.sub.3 4-CH.sub.3, 3-OCH.sub.2 C.sub.6 H.sub.5                      4-F, 3-OCF.sub.2 Br 4-CH.sub.3, 3-cyclopentyloxy                              4-F, 3-OCF.sub.2 H 4-CH.sub.3, 3-cyclohexyloxy                                4-F, 3-OCF.sub.2 CF.sub.2 H 2-Cl, 5-OCH.sub.3                                 4-F, 3-OCF.sub.2 CFHCF.sub.3 2-Cl, 5-OCH.sub.2 CH.sub.3                       4-F, 3-OCH.sub.2 CF.sub.3 2-Cl, 5-OCH.sub.2 CH.sub.2 CH.sub.3                 4-F, 3-OC.sub.6 H.sub.5 2-Cl, 5-OCH(CH.sub.3).sub.2                         ______________________________________                                    

                  TABLE 19                                                        ______________________________________                                        2-Cl, 5-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                    2-Cl, 4-OCF.sub.2 CF.sub.2 H                                   2-Cl, 5-OCH(CH.sub.3)CH.sub.2 CH.sub.3 2-Cl, 4-OCF.sub.2 CFHCF.sub.3                          2-Cl, 5-OCH.sub.2 CH(CH.sub.3).sub.2 2-Cl, 4-OCH.sub.2                       CF.sub.3                                                       2-Cl, 5-OC(CH.sub.3).sub.3 2-Cl, 4-OC.sub.6 H.sub.5                           2-Cl, 5-OCF.sub.3 2-Cl, 4-OCH.sub.2 C.sub.6 H.sub.5                           2-Cl, 5-OCF.sub.2 Br 2-Cl, 4-cyclopentyloxy                                   2-Cl, 5-OCF.sub.2 H 2-Cl, 4-cyclohexyloxy                                     2-Cl, 5-OCF.sub.2 CF.sub.2 H 4-OCH.sub.3, 3-OCH.sub.2 CH.sub.2 CH.sub.3       2-Cl, 5-OCF.sub.2 CFHCF.sub.3 4-OCH.sub.3, 3-OCH(CH.sub.3).sub.2                              2-Cl, 5-OCH.sub.2 CF.sub.3 4-OCH.sub.3, 3-OCH.sub.2                          (CH.sub.2).sub.2 CH.sub.3                                      2-Cl, 5-OC.sub.6 H.sub.5 4-OCH.sub.3, 3-OCH(CH.sub.3)CH.sub.2 CH.sub.3                        2-Cl, 5-OCH.sub.2 C.sub.6 H.sub.5 4-OCH.sub.3, 3-OCH.sub                     .2 CH(CH.sub.3).sub.2                                          2-Cl, 5-cyclopentyloxy 4-OCH.sub.3, 3-OC(CH.sub.3)hd 3                        2-Cl, 5-cyclohexyloxy 4-OCH.sub.3, 3-OCF.sub.3                                2-Cl, 4-OCH.sub.3 4-OCH.sub.3, 3-OCF.sub.2 Br                                 2-Cl, 4-OCH.sub.2 CH.sub.3 4-OCH.sub.3, 3-OCF.sub.2 H                         2-Cl, 4-OCH.sub.2 CH.sub.2 CH.sub.3 4-OCH.sub.3, 3-OCF.sub.2 CF.sub.2 H       2-Cl, 4-OCH(CH.sub.3).sub.2 4-OCH.sub.3, 3-OCF.sub.2 CFHCF.sub.3                              2-Cl, 4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3 4-OCH.sub.3,                      3-OCH.sub.2 CF.sub.3                                          2-Cl, 4-OCH(CH.sub.3)CH.sub.2 CH.sub.3 4-OCH.sub.3, 3-OC.sub.6 H.sub.5                        2-Cl, 4-OCH.sub.2 CH(CH.sub.3).sub.2 4-OCH.sub.3,                            3-OCH.sub.2 C.sub.6 H.sub.5                                    2-Cl, 4-OC(CH.sub.3).sub.3 4-OCH.sub.3, 3-cyclopentyloxy                      2-Cl, 4-OCF.sub.3 4-OCH.sub.3, 3-cyclohexyloxy                                2-Cl, 4-OCF.sub.2 Br 2,5-(CH.sub.3).sub.2, 4-OCH.sub.3                        2-Cl, 4-OCF.sub.2 H 2,5-(CH.sub.3).sub.2, 4-OCH.sub.2 CH.sub.3              ______________________________________                                    

                  TABLE 20                                                        ______________________________________                                        2,5-(CH.sub.3).sub.2, 4-OCH.sub.2 CH.sub.2 CH.sub.3                                             3,5-(CH.sub.3).sub.2,                                         2,5-(CH.sub.3).sub.2, 4-OCH(CH.sub.3).sub.2 4-OCH.sub.2 (CH.sub.2).sub.2                       CH.sub.3                                                     2,5-(CH.sub.3).sub.2, 3,5-(CH.sub.3).sub.2,                                   4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3 4-OCH(CH.sub.3)CH.sub.2 CH.sub.3                         2,5-(CH.sub.3).sub.2, 3,5-(CH.sub.3).sub.2, 4-OCH.sub.2                       CH(CH.sub.3).sub.2                                           4-OCH(CH.sub.3)CH.sub.2 CH.sub.3 3,5-(CH.sub.3).sub.2, 4-OC(CH.sub.3).su                      b.3                                                           2,5-(CH.sub.3).sub.2, 3,5-(CH.sub.3).sub.2, 4-OCF.sub.3                       4-OCH.sub.2 CH(CH.sub.3).sub.2 3,5-(CH.sub.3).sub.2, 4-OCF.sub.2 Br                            2,5-(CH.sub.3).sub.2, 4-OC(CH.sub.3).sub.3 3,5-(CH.sub.                      3).sub.2, 4-OCF.sub.2 H                                       2,5-(CH.sub.3).sub.2, 4-OCF.sub.3 3,5-(CH.sub.3).sub.2, 4-OCF.sub.2                           CF.sub.2 H                                                    2,5-(CH.sub.3).sub.2, 4-OCF.sub.2 Br 3,5-(CH.sub.3).sub.2, 4-OCF.sub.2                        CFHCF.sub.3                                                   2,5-(CH.sub.3).sub.2, 4-OCF.sub.2 H 3,5-(CH.sub.3).sub.2, 4-OCH.sub.2                         CF.sub.3                                                      2,5-(CH.sub.3).sub.2, 4-OCF.sub.2 CF.sub.2 H 3,5-(CH.sub.3).sub.2,                            4-OC.sub.6 H.sub.5                                            2,5-(CH.sub.3).sub.2, 4-OCF.sub.2 CFHCF.sub.3 3,5-(CH.sub.3).sub.2,                           4-OCH.sub.2 C.sub.6 H.sub.5                                   2,5-(CH.sub.3).sub.2, 4-OCH.sub.2 CF.sub.3 3,5-(CH.sub.3).sub.2,                               2,5-(CH.sub.3).sub.2, 4-OC.sub.6 H.sub.5 4-cyclopentylo                      xy                                                            2,5-(CH.sub.3).sub.2, 4-OCH.sub.2 C.sub.6 H.sub.5 3,5-(CH.sub.3).sub.2,       2,5-(CH.sub.3).sub.2, 4-cyclohexyloxy                                         4-cyclopentyloxy 3,5-Cl.sub.2, 4-OCH.sub.3                                    2,5-(CH.sub.3).sub.2, 3-OC.sub.6 H.sub.4 (p-F)                                4-cyclohexyloxy 3,5-Cl.sub.2, 4-OCH.sub.2 CH.sub.3                            3,5-(CH.sub.3).sub.2, 4-OCH.sub.3 3,5-Cl.sub.2, 4-OCH.sub.2 CH.sub.2                          CH.sub.3                                                      3,5-(CH.sub.3).sub.2, 4-OCH.sub.2 CH.sub.3 3,5-Cl.sub.2, 4-OCH(CH.sub.3)                      .sub.2                                                        3,5-(CH.sub.3).sub.2, 4-OCH.sub.2 CH.sub.2 CH.sub.3 3,5-Cl.sub.2,                             4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3                         3,5-(CH.sub.3).sub.2, 4-OCH(CH.sub.3).sub.2 3,5-Cl.sub.2, 4-OCH(CH.sub.3                      )CH.sub.2 CH.sub.3                                          ______________________________________                                    

                                      TABLE 21                                    __________________________________________________________________________             3,5-Cl.sub.2, 4-OCH.sub.2 CH(CH.sub.3).sub.2                                                      3,5-Cl.sub.2, 4-OC.sub.6 H.sub.5                   3,5-Cl.sub.2, 4-OC(CH.sub.3).sub.3 3,5-Cl.sub.2, 4-OCH.sub.2 C.sub.6                                     H.sub.5                                            3,5-Cl.sub.2, 4-OCF.sub.3 3,5-Cl.sub.2, 4-cyclopentyloxy                      3,5-Cl.sub.2, 4-OCF.sub.2 Br 3,5-Cl.sub.2, 4-cyclohexyloxy                    3,5-Cl.sub.2, 4-OCF.sub.2 H 2-F, 5-OC.sub.6 H.sub.4 (p-F)                     3,5-Cl.sub.2, 4-CF.sub.2 CF.sub.2 H 2-Br, 5-(OC.sub.6 H.sub.5)                3,5-Cl.sub.2, 4-OCF.sub.2 CFHCF.sub.3 4-OC.sub.6 H.sub.4 (p-CF.sub.3)                                     3,5-Cl.sub.2, 4-OCH.sub.2 CF.sub.3 3-OC.sub.                                 6 H.sub.4 (p-F)                                    3,4-OCH.sub.2 CH.sub.2 O--, 2-CH.sub.3                                      __________________________________________________________________________                                   #STR52##                                                                      , TR53##                                                                      #STR54##                                          -                                                                                                         , TR55##                                                                      #STR56##                                          -                                                                                                         , TR57##                                                                      #STR58##                                          -                                                                                                         , TR59##                                                                      #STR60##                                          -                                                                                                         , TR61##                                                                      #STR62##                                          -                                                                                                         , TR63##                                                                      #STR64##                                          -                                                                                                         , TR65##                                                                      #STR66##                                          -                                                                                                          STR67##                                                                      , TR68##                                                                      #STR69##                                          -                                                                                                         , TR70##                                                                      #STR71##                                          -                                                                                                         , TR72##                                                                      #STR73##                                          -                                                                                                         , TR74##                                                                      #STR75##                                          -                                                                                                         , TR76##                                                                      #STR77##                                          -                                                                                                         , TR78##                                                                      #STR79##                                          -                                                                                                         , TR80##                                                                     ##STR81##                                       __________________________________________________________________________

(in which the position of the heterocyclic ring and (R₁₆)_(s) are eachas defind in Table 22).

                  TABLE 22                                                        ______________________________________                                        Position of                                                                     heterocyclic ring (R                                                                             .sub.16).sub.s                                           ______________________________________                                          3 H                                                                           3 6-Cl                                                                        3 6-Br                                                                        3 6-I                                                                         3 6-CH.sub.3                                                                  3 6-CF.sub.3                                                                  3 2-Cl, 6-CH.sub.3                                                            3 5,6-Cl.sub.2                                                                3 5-Br                                                                        3 5,6-(OCH.sub.3).sub.2                                                       2 H                                                                           2 6-CH.sub.3                                                                  2 6-Cl                                                                        2 5-CF.sub.3                                                                  2 5-Cl                                                                        2 6-F                                                                         2 5-Br                                                                        2 3,5-(CF.sub.3).sub.2                                                        2 4,5-(CF.sub.3).sub.2                                                        2 3,5-Cl.sub.2                                                                2 3-Cl, 5-CF.sub.3                                                            4 H                                                                         ______________________________________                                                        #STR82##                                                                      #STR83##                                                         -                                                                                          #STR84##                                                         -                                                                                          #STR85##                                                         -                                                                                          #STR86##                                                         -                                                                                          #STR87##                                                         -                                                                                          #STR88##                                                         -                                                                                          #STR89##                                                         -                                                                                         ##STR90##                                                      ______________________________________                                    

(in which G, the position of the heterocyclic ring and (R₁₆)_(s) areeach as defined in Tables 23 and 24).

                  TABLE 23                                                        ______________________________________                                                 Position of                                                             heterocyclic                                                                 G ring (R.sub.16).sub.5                                                     ______________________________________                                        O        2                 H                                                    O 2 5-CH.sub.3                                                                O 2 5-CH.sub.2 OCH.sub.3                                                      O 2 5-CH.sub.2 CH.sub.3                                                       O 2 5-NO.sub.2                                                                O 2 5-Cl                                                                      O 2 5-Br                                                                      O 3 H                                                                         O 3 2-CH.sub.3                                                                O 3 2,5-(CH.sub.3).sub.2                                                      O 3 2,4-(CH.sub.3).sub.2                                                      S 2 H                                                                         S 2 5-CH.sub.3                                                                S 2 5-Cl                                                                      S 2 5-Br                                                                      S 2 5-NO.sub.2                                                                S 2 5-NHCOCH.sub.3                                                            S 2 5-NHCOCF.sub.3                                                            S 2 3-CH.sub.3                                                                S 2 4-Br                                                                      S 3 H                                                                         S 3 2,5-(CH.sub.3).sub.2                                                      NH 2 H                                                                      ______________________________________                                    

                  TABLE 24                                                        ______________________________________                                                Position of                                                              heterocyclic                                                                 G ring (R.sub.16).sub.s                                                     ______________________________________                                          NH 2 2,4-(CH.sub.3).sub.2                                                     N 2 1-CH.sub.3                                                                NH 2 3,5-(CH.sub.3).sub.2                                                     NH 2 3,4,5-(CH.sub.3).sub.3                                                   NH 2 3,4-(C.sub.2 H.sub.5).sub.2, 5-CH.sub.3                                  NH 3 H                                                                        N 3 1-CH.sub.3                                                                NH 3 5-Cl                                                                     N 2 1,2,4-(CH.sub.3).sub.3                                                    N 2 1,3,5-(CH.sub.3).sub.3                                                    N 2 1,3,4,5-(CH.sub.3).sub.4                                                  N 2 3,4-(C.sub.2 H.sub.5).sub.2, 1,5-(CH.sub.3).sub.2                         N 3 5-Cl, 1-CH.sub.3                                                        ______________________________________                                                        #STR91##                                                                      #STR92##                                                         -                                                                                          #STR93##                                                         -                                                                                          #STR94##                                                         -                                                                                         ##STR95##                                                      ______________________________________                                    

(in which G₁, G₂, the position of heterocyclic ring and (R₁₆)_(s) areeach as defined in Table 25).

                  TABLE 25                                                        ______________________________________                                                        Position of                                                       heterocyclic                                                                G.sub.1 G.sub.2 ring (R.sub.16).sub.s                                       ______________________________________                                          O N 3 H                                                                       O N 3 5-Cl                                                                    O N 3 5-Br                                                                    O N 5 H                                                                       S N 3 H                                                                       S N 3 5-Cl                                                                    S N 3 5-Br                                                                    NH N 4 H                                                                      NH N 4 3-CF.sub.3                                                             N N 5 1-C.sub.2 H.sub.5, 3-CH.sub.3                                           NH N 5 3-CH.sub.3                                                             N N 4 1-CH.sub.3                                                              N N 4 1-CH.sub.3, 3-CF.sub.3                                                  N N 5 1,3-(CH.sub.3).sub.2                                                    N N 4 1-CH.sub.3, 5-NO.sub.2                                                ______________________________________                                                        #STR96##                                                                      #STR97##                                                         -                                                                                          #STR98##                                                         -                                                                                          #STR99##                                                         -                                                                                          #STR100##                                                        -                                                                                         ##STR101##                                                     ______________________________________                                    

(in which G₁, G₂, the position of heterocyclic ring and (R₁₆)_(s) areeach as defined in Table 26).

                                      TABLE 26                                    __________________________________________________________________________                   Position of                                                      G.sub.1 G.sub.2 heterocyclic ring (R.sub.16).sub.s                          __________________________________________________________________________      S N 4 H                                                                       S N 4 2-Cl                                                                    S N 4 2-Br                                                                    S N 5 H                                                                       S N 5 2-Cl                                                                    S N 5 2-Br                                                                    S N 5 4-CH.sub.3                                                              NH N 5 2,4-(CH.sub.3).sub.2                                                   NH N 2 H                                                                      NH N 5 3-CH.sub.3                                                             N N 5 1-C.sub.2 H.sub.5, 3-CH.sub.3                                           N N 2 1-CH.sub.3                                                              N N 5 1,3-(CH.sub.3).sub.2                                                    S N 2 5-Br                                                                  __________________________________________________________________________                                  #STR102##                                                                     , TR103##                                                                     #STR104##                                          -                                                                                                        , TR105##                                                                    ##STR106##                                       __________________________________________________________________________

                                      TABLE 27                                    __________________________________________________________________________              Position of heterocyclic ring                                                              (R.sub.16).sub.s                                       __________________________________________________________________________      3 H                                                                         __________________________________________________________________________                                  #STR107##                                                                     #STR108##                                                                     #STR109##                                          -                                                                                                        , TR110##                                                                    ##STR111##                                       __________________________________________________________________________

                                      TABLE 28                                    __________________________________________________________________________              Position of heterocyclic ring                                                              (R.sub.16).sub.s                                       __________________________________________________________________________      3 1-H                                                                         3 1-C.sub.6 H.sub.5                                                         __________________________________________________________________________                                  #STR112##                                                                     , TR113##                                                                     #STR114##                                          -                                                                                                        , TR115##                                                                    ##STR116##                                       __________________________________________________________________________

                                      TABLE 29                                    __________________________________________________________________________               Position of heterocyclic ring                                                              (R.sub.16).sub.s                                      __________________________________________________________________________      3 6-Cl                                                                        4 H                                                                         __________________________________________________________________________                                     #STR117##                                                                     , TR118##                                                                     #STR119##                                       -                                                                                                           , TR120##                                                                    ##STR121##                                    __________________________________________________________________________

                                      TABLE 30                                    __________________________________________________________________________               Position of heterocyclic ring                                                              (R.sub.16).sub.s                                      __________________________________________________________________________      2 5-Br                                                                        5 2-Cl                                                                      __________________________________________________________________________                                     #STR122##                                                                     , TR123##                                                                     #STR124##                                       -                                                                                                           , TR125##                                                                    ##STR126##                                    __________________________________________________________________________

                                      TABLE 31                                    __________________________________________________________________________               Position of heterocyclic ring                                                              (R.sub.16).sub.s                                      __________________________________________________________________________      2 H                                                                           2 5-CH.sub.3                                                                __________________________________________________________________________                                     #STR127##                                                                     , TR128##                                                                     #STR129##                                       -                                                                                                           , TR130##                                                                    ##STR131##                                    __________________________________________________________________________

                                      TABLE 32                                    __________________________________________________________________________              Position of heterocyclic ring                                                              (R.sub.16).sub.s                                       __________________________________________________________________________      3 5,6-(CH.sub.3).sub.2                                                      __________________________________________________________________________                                     #STR132##                                                                     , TR133##                                                                     #STR134##                                       -                                                                                                           , TR135##                                                                    ##STR136##                                    __________________________________________________________________________

                  TABLE 33                                                        ______________________________________                                        Position of heterocyclic ring                                                                    (R.sub.16).sub.s                                           ______________________________________                                          2 4,6-(C.sub.6 H.sub.5).sub.2                                                 5 4,6-(CCl.sub.3).sub.2                                                     ______________________________________                                                        , TR137##                                                                     #STR138##                                                        -                                                                                          #STR139##                                                        -                                                                                          #STR140##                                                        -                                                                                         ##STR141##                                                     ______________________________________                                    

                  TABLE 34                                                        ______________________________________                                                                      #STR142##                                                                     #STR143##                                                                    ##STR144##                                       ______________________________________                                                                      #STR145##                                                                     #STR146##                                        ##STR147##                                                                               ##STR148##                                                           -                                                                                                        #STR149##                                                                     #STR150##                                          -                                                                                                        #STR151##                                                                     #STR152##                                          -                                                                                                        #STR153##                                                                     #STR154##                                          -                                                                                                        #STR155##                                                                     #STR156##                                          -                                                                                                        #STR157##                                                                     #STR158##                                          -                                                                                                       ##STR159##                                       ______________________________________                                    

The compounds of general formula [IV] or [V], which are intermediatesfor the production of the present compounds, can be produced, forexample, according to the following schemes 1 to 4: ##STR160##

The compounds of general formula [VI] and the alcohol compounds ofgeneral formula [VII], which are intermediates for the production of thepresent compounds, can be obtained from commercial sources or can beproduced according to the following scheme 5: ##STR161## wherein L₆ ismesyloxy or tosyloxy, and L₃ and X are each as defined above.

The aldehyde compounds of general formula [VIII], which areintermediates for the production of the present compounds, can beproduced, for example, according to the following scheme 6: ##STR162##wherein all the symbols are each as defined above.

The compounds of general formula [IX], which are intermediates for theproduction of the present compounds, can be produced, for example,according to the following scheme 7: ##STR163##

The compounds of general formula [XVIII] wherein Y and Z are bothoxygen, which are intermediates for the production of the presentcompounds, can be produced, for example, according to the followingschemes 8.1 and 8.2: ##STR164## wherein R₂, R₃, R₄, R₅, R₆, R₇, X, L₂,L₄, m and n are each as defined above; L₇ hydroxyl, halogen, (e.g.,chlorine, bromine, iodine), mesyl or tosyl; R₂₁ is a protecting groupfor alcohols (e.g., benzoyl); and R₂₂ is C₁ -C₄ alkoxy (e.g., methoxy,ethoxy).

The compounds of general formula [III], [XII], [XIV] or [XVII], whichare intermediates for the production of the present compounds, can beproduced, for example, according to the following schemes 9.1, 9.2 and10: ##STR165## wherein R₂, R₃, R₄, R₅, R₆, R₇, R₁₃, X, Y, Z, L₃, L₄, mand n are each as defined above; L₅ is methyl, ethyl or propyl; L₇ ishydroxyl, halogen (e.g., chlorine, bromine, iodine), mesyl or tosyl; R₂₁is a protecting group for alcohols (e.g., benzoyl); and R₂₂ is C₁ -C₄alkoxy (e.g., methoxy, ethoxy). ##STR166## wherein R₂, R₃, R₄, R₅, R₆,R₇, R₁₃, X, Y, m and n are each as defined above.

The compounds of general formula [XIII], [XV], [XVI], [XIX] or [XXII],which are intermediates for the production of the present compounds, canbe obtained from commercial sources or can be produced, for example,according to the following scheme 11 or 12: ##STR167## wherein R₂₁ ismethoxy, ethoxy, propoxy or imidazolyl, and the other variables are eachas defined above. ##STR168##

The present compounds are satisfactorily effective for the control ofvarious noxious insects, examples of which are as follows:

Hemiptera

Delphacidae such as Laodelphax striatellus, Nilaparvata lugens andSogatella furcifera, Deltocephalidae such as Nephotettix cincticeps andNephotettix virescens, Aphididae, Pentatomidae, Aleyrodidae , Coccidae,Tingidae, Psyllidae, etc.

Lepidoptera

Pyralidae such as Chilo suppressalis, Cnaphalocrocis medinalis, Ostrinianubilalis, Parapediasia teterrella, Notarcha derogata and Plodiainterpunctella, Noctuidae such as Spodoptera litura, Spodoptera exigua,Spodoptera littoralis, Pseudaletia separata, Mamestra brassicae, Agrotisipsilon, Trichoplusia spp., Heliothis spp. and Helicoverpa spp.,Pieridae such as Pieris rapae crucivora, Tortricidae such as Adoxophyesspp., Grapholita molesta and Cydia pomonella, Carposinidae such asCarposina niponensis, Lyonetiidae such as Lyonetia spp., Lymantriidaesuch as Lymantria spp. and Euproctis spp., Yponomeutidae such asPlutella xylostella, Gelechiidae such as Pectinophora gossypiella,Arctiidae such as Hyphantria cunea, Tineidae such as Tinea translucensand Tineola bisselliella, etc.

Diptera

Culex such as Culex pipiens pallens and Cules tritaeniorhynchus, Aedessuch as Aedes aegypti and Aedes albopictus, Anopheles such asAnophelinae sinensis, Chironomidae, Muscidae such as Musca domestica andMuscina stabulans, Calliphoridae, Sarcophagidae, Fannia canicularis,Anthomyiidae such as Delia Platura and Delia antigua, Trypetidae,Drosophilidae, Psychodidae, Simuliidae, Tabanidae, Stomoxyinae,Agromyzidae, etc.

Coleoptera

Diabrotica such as Diabrotica virgifera and Diabrotica undecimpunctata,Scarabaeidae such as Anomala cuprea and Anomala rufocuprea,Curculionidae such as Sitophilus zeamais, Lissorphoptrus oryzophilus,Hypera pastica, and Calosobruchys chinensis, Tenebrionidae such asTenebrio molitor and Tribolium castaneum, Chrysomelidae such asAulacophora femoralis, Phyllotreta striolata, Anobiidae andLeoptinotarsa decemlineata, Anobiidae, Epilachna spp. such as Epilachnavigintioctopunctata, Lyctidae, Bostrychidae, Cerambycidae, Paederusfuscipes, etc.

Dictyoptera

Blattella germanica, Periplaneta fuliginosa, Peroplaneta americana,Periplaneta brunnea, Blatta orientalis, etc.

Thysanoptera

Thrips palmi, Thrips tabaci, Thrips hawaiiensis, etc.

Hymenoptera

Formicidae, Vespidae, Bethylidae, Tenthredinidae such as Athalia rosaejaponensis, etc.

Orthoptera

Gryllotalpidae, Acrididae, etc.

Siphonaptera

Purex irritans etc.

Anoplura

Pediculus humanus capitis, Phthirus pubis, etc.

Isoptera (Termites)

Reticulitermes speratus, Coptotermes formosanus, etc.

The present compounds are also effective for the control of variousnoxious insects having resistance to conventional insecticides.

When the present compounds are used as active ingredients ofinsecticides, they may be used as such without any addition of otheringredients. The present compounds are, however, usually formulated intodosage forms such as oil sprays, emulsifiable concentrates, wettablepowders, flowables, granules, dusts, aerosols, fumigants (foggings) andpoison baits. These dosage forms are usually prepared by mixing thepresent compounds with solid carriers, liquid carriers, gaseous carriersor baits, and if necessary, adding surfactants and other auxiliariesused for formulation.

Each of the dosage forms usually contains at least one of the presentcompounds as an active ingredient in an amount of 0.01% to 95% byweight.

Examples of the solid carrier to be used for formulation are fine powderor granules of clay materials such as kaolin clay, diatomaceous earth,synthetic hydrated silicon oxide, bentonite, Fubasami clay and acidclay; various kinds of talc, ceramics and other inorganic minerals suchas sericite, quartz, sulfur, active carbon, calcium carbonate andhydrated silica; and chemical fertilizers such as ammonium sulfate,ammonium phosphate, ammonium nitrate, urea and ammonium chloride.

Examples of the liquid carrier are water; alcohols such as methanol andethanol; ketones such as acetone and methyl ethyl ketone; aromatichydrocarbons such as benzene, toluene, xylene, ethylbenzene andmethylnaphthalene; aliphatic hydrocarbons such as hexane, cyclohexane,kerosine and gas oil; esters such as ethyl acetate and butyl acetate;nitriles such as acetonitrile and isobutyronitrile; ethers such asdiisopropyl ether and dioxane; acid amides such as N,N-dimethylformamideand N,N-dimethylacetamide; halogenated hydrocarbons such asdichloromethane, trichloroethane and carbon tetrachloride; dimethylsulfoxide; and vegetable oils such as soybean oil and cottonseed oil.

Examples of the gaseous carrier or propellant are flon gas, butane gas,LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide.

Examples of the surfactant are alkyl sulfates, alkyl sulfonates, alkylarylsulfonates, alkyl aryl ethers and their polyoxyethylene derivatives,polyethylene glycol ethers, polyhydric alcohol esters and sugar alcoholderivatives.

Examples of the auxiliaries used for formulation, such as fixing agentsor dispersing agents, are casein, gelatin, polysaccharides such asstarch, gum arabic, cellulose derivatives and alginic acid, ligninderivatives, bentonite, sugars, and synthetic water-soluble polymerssuch as polyvinyl alcohol, polyvinyl pyrrolidone and polyacrylic acid.

Examples of the stabilizer are PAP (isopropyl acid phosphate), BHT(2,6-di-tert-butyl-4-methylphenol), BHA (mixtures of2-t-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetableoils, mineral oils, surfactants, fatty acids and their esters.

Examples of the base material to be used in the poison baits are baitmaterials such as grain powder, vegetable oils, sugars and crystallinecellulose; antioxidants such as dibutylhydroxytoluene andnordihydroguaiaretic acid; preservatives such as dehydroacetic acid;substances for preventing erroneous eating, such as red pepper powder,attractant flavors such as cheese flavor or onion flavor.

The dosage forms thus obtained are used as such or after diluted withwater. The dosage forms may also be used in combination with otherinsecticides, nematocides, acaricides, bactericides, fungicides,herbicides, plant growth regulators, synergists, fertilizers, soilconditioners and/or animal feed under non-mixing conditions orpre-mixing conditions.

Examples of the insecticide, acaricide and/or nematocide which can beused are organophosphorus compounds such as Fenitrothion [O,O-dimethylO-(3-methyl-4-nitrophenyl)phosphorothioate], Fenthion [O,O-dimethylO-(3-methyl-4-methylthio)phenyl)phophorothioate], Diazinon[O,O-diethyl-O-2-isopropyl-6-methylpyrimidin-4-yl-phosphorothioate],Chlorpyriphos [O,O-diethyl-O-3,5,6-trichloro-2-pyridylphosphorothioate],Acephate [O,S-dimethylacetylphosphoramidothioate], Methidathion[S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethylO,O-dimethylphosphorodithioate], Disulfoton [O,O-diethylS-2-ethylthioethylphosphorothioate], DDVP[2,2-dichlorovinyldimethylphosphate], Sulprofos [O-ethylO-4-(methylthio)phenyl S-propyl phosphorodithioate], Cyanophos[O-4-cyanophenyl O,O-dimethylphosphorothioate], Dioxabenzofos[2-methoxy-4H-1,3,2-benzodioxaphosphinine-2-sulfide], Dimethoate[O,O-dimethyl-S-(N-methylcarbamoylmethyl)dithiophosphate], Phenthoate[ethyl 2-dimethoxyphosphinothioylthio(phenyl)acetate], Malathion[diethyl(dimethoxyphosphinothioylthio)succinate], Trichlorfon [dimethyl2,2,2-trichloro-1-hydroxyethylphosphonate], Azinphos-methyl[S-3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethylO,O-dimethylphosphorodithioate], Monocrotophos [dimethyl(E)-1-methyl-2-(methylcarbamoyl)vinylphosphate], Ethion[O,O,O',O'-tetraethyl S,S'-methylenebis(phosphorodithioate)] andProfenofos [O-4-bromo-2-chlorophenyl O-ethyl S-propyl phosphorothioate];carbamate compounds such as BPMC [2-sec-butylphenylmethylcarbamate],Benfuracarb [ethylN-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl(methyl)aminothio]-N-isopropyl-β-alaninate],Propoxur [2-isopropoxyphenyl N-methylcarbamate], Carbosulfan[2,3-dihydro-2,2-dimethyl-7-benzo[b]furanylN-dibutylaminothio-N-methylcarbamate], Carbaril[1-naphthyl-N-methylcarbamate], Methomyl[S-methyl-N-[(methylcarbamoyl)oxy]thioacetimidate], Ethiofencarb[2-(ethylthiomethyl)phenylmethylcarbamate], Aldicarb[2-methyl-2-(methylthio)propanaldehyde O-methylcarbamoyloxime], Oxamyl[N,N-di-methyl-2-methylcarbamoyloxyimino-2-(methylthio)acetamide],Fenothiocarb [S-(4-phenoxybutyl)-N,N -dimethylthiocarbamate], Thiodicarb[3,7,9,13-tetramethyl-5,11-dioxa-2,8,14-trithia-4,7,9,12-tetraazapentadeca-3,12-diene-6,10-dione]and Alanylcarb [ethyl(Z)-N-benzyl-N-{[methyl(1-methylthioethylideneaminooxycarbonyl)amino]thio}-β-alaninate]; pyrethroid compounds such as Etofenprox[2-(4-ethoxyphenyl)-2-methyl-propyl-3-phenoxybenzylether], Fenvalerate[(RS)-α-cyano-3-phenoxybenzyl (RS)-2-(4-chlorophenyl)-3-methylbutyrate],Esfenvalerate [(S)-α-cyano-3-phenoxybenzyl(S)-2-(4-chlorophenyl)-3-methylbutyrate], Fenpropathrin[(RS)-α-cyano-3-phenoxybenzyl2,2,3,3-tetramethylcyclopropanecarboxylate], Cypermethrin[(RS)-α-cyano-3-phenoxybenzyl(1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate],Permethrin[3-phenoxybenzyl(1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate],Cyhalothrin [(RS)-α-cyano-3-phenoxybenzyl(Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate],Deltamethrin [(S)-α-cyano-m-phenoxybenzyl(1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate],Cycloprothrin [(RS)-α-cyano-3-phenoxybenzyl(RS)-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate],Fluvalinate [α-cyano-3-phenoxybenzylN-(2-chloro-α,α,α-trifluoro-p-tolyl)-D-valinate], Bifenthrin[2-methylbiphenyl-3-yl-methyl)(Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate],Acrinathrin [(S)-α-cyano-(3-phenoxyphenyl)methyl[1R-{1α(S*),3α(Z)}]-2,2-dimethyl-3-[3-oxo-3-(2,2,2-trifluoro-1-(trifluoromethyl)ethoxy-1-propenyl]cyclopropanecarboxylate],2-methyl-2-(4-bromodifluoromethoxyphenyl)propyl (3-phenoxybenzyl) ether,Traromethrin[(S)-α-cyano-3-phenoxylbenzyl(1R,3R)-3-[(1'RS)-(1',1',2',2'-tetrabromoethyl)]-2,2-dimethylcyclopropanecarboxylate]and Silafluofen [4-ethoxylphenyl[3-(4-fluoro-3-phenoxyphenyl)propyl]dimethylsilane]; thiadiazinederivatives such as Buprofezin[2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazin-4-one];nitroimidazolidine derivatives such as Imidacloprid[1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylidenamine];Nereistoxin derivatives such as Cartap[S,S'-(2-dimethylaminotrimethylene)bisthiocarbamate], Thiocyclam[N,N-dimethyl-1,2,3-trithian-5-ylamine] and Bensultap[S,S'-2-dimethylaminotrimethylene di(benzenethiosulfonate)];N-cyanoamnidine derivatives such as acetariprid[N-cyano-N'-methyl-N'-(6-chloro-3-pyridylmethyl)acetamidine];chlorinated hydrocarbon compounds such as Endosulfan[6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepinoxide],γ-BHC [1,2,3,4,5,6-hexachlorocyclohexane] and Kelthane[1,1-bis(chlorophenyl)-2,2,2-trichloroethanol]; benzoylphenylureacompounds such as Chlorfluazuron[1-(3,5-dichloro-4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)phenyl)-3-(2,6-difluorobenzoyl)urea],Teflubenzuron[1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea] andFulphenoxron[1-(4-(2-chloro-4-trifluoromethylphenoxy)-2-fluorophenyl)-3-(2,6-difluorobenzoyl)urea];formamidine derivatives such as Amitraz[N,N'-[(methylimino)dimethylidine]-di-2,4-xylidine] and Chlordimeform[N'-(4-chloro-2-methylphenyl)-N,N-dimethylmethanimidamide]; thioureaderivatives such as Diafenthiuron[N-(2,6-diisopropyl-4-phenoxyphenyl)N'-tert-butylcarbodiimide];Bromopropylate [isopropyl 4,4'-dibromobenzylate], Tetradifon[4-chlorophenyl-2,4,5-trichlorophenylsulfone], Quinomethionate[S,S-6-methylquinoxaline-2,3-diyldithiocarbonate], Propargite[2-(4-tert-butylphenoxy)cyclohexylprop-2-yl sulfite], Fenbutatin oxide[bis[tris(2-methyl-2-phenylpropyl)tin]oxide], Hexythiazox[(4RS,5RS)-5-(4-chlorophenyl)-N-chlorohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide],Chlofentezine [3,6-bis(2-chlorophenyl)-1,2,4,5-tetrazine], Pyridaben[2-tert-butyl-5-(4-tert-butylbenzylthio)-4-chloropyridazin-3(2H)-one],Fenpyroximate [tert-butyl(E)-4-[(1,3-dimethyl-5-phenoxypyrazol-4-yl)methyleneaminooxymethyl]benzoate],Tebfenpyrad[N-4-tert-butylbenzyl)-4-chloro-3-ethyl-1-methyl-5-pyrazolecarboxamide],polynactin complexes including tetranactin, dinactin and trinactin;Milbemectin, Avermectin, Ivermectin, Azadilactin [AZAD], Pyrimidifen[5-chloro-N-[2-{4-(2-ethoxyethyl)-2,3-dimethylphenoxy}ethyl]-6-ethylpyrimidin-4-amine],Chlorfenapyl[4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethylpyrrole-3-carbonitrile],Tebfenozide[N-tert-butyl-N'-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide], Fipronyl[5-amino-1-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitrite]and Pimetrozine[2,3,4,5-tetrahydro-3-oxo-4-[(pyridin-3-yl)-methyleneamino]-6-methyl-1,2,4-triazine].

When the present compounds are used as active ingredients ofinsecticides for agriculture, the application amount thereof is usuallyin the range of 0.1 to 100 g per 10 ares. In the case of emulsifiableconcentrates, wettable powders and flowable concentrates, which are usedafter diluted with water, the application concentration thereof isusually in the range of 0.1 to 500 ppm. In the case of granules anddusts, they are applied as such without any dilution. When the presentcompounds are used as active ingredients of insecticides for epidemicprevention, they are formulated into dosage forms such as emulsifiableconcentrates, wettable powders and flowable concentrates, which areapplied after diluted with water to a typical concentration of 0.1 to500 ppm; or they are formulated into dosage forma such as oil sprays,aerosols, fumigants and poisonous baits, which are applied as suchwithout any dilution.

The application amount and application concentration may vary dependingupon various conditions such as dosage form type, application time,place and method, kind of noxious insects, and degree of damage, andthey can be increased or decreased without limitation to the aboverange.

The present invention will be further illustrated by the followingproduction examples, formulation examples and test examples; however,the present invention is not limited to these examples.

The following are production examples for the present compoundsaccording to various production processes.

PRODUCTION EXAMPLE 1

Production of Compound (2) by Production Process F

To a solution of 0.21 g of3,5-dichloro-4-(3-aminopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzeneand 0.07 g of triethylamine dissolved in 5 ml of dichloromethane wasadded dropwise a solution of 0.11 g of 4-chlorobenzoyl chloridedissolved in 5 ml of dichloromethane, while stirring under ice cooling.After stirring at room temperature for 6 hours, the reaction mixture waswashed with water and then concentrated to give a residue. The residuewas subjected to silica gel chromatography, which afforded 0.21 g of3,5-dichloro-4-(3-(4-chlorobenzamido)propyloxy)-1-(3,3-dichloro-2-propenyl-oxy)benzene(71% yield), m.p., 95.1° C.

PRODUCTION EXAMPLE 2

Production of Compound (7) by Production Process F

To a solution of 0.21 g of3,5-dichloro-4-(3-aminopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzeneand 0.07 g of triethylamine dissolved in 5 ml of dichloromethane wasadded dropwise a solution of 0.15 g of 4-trifluoromethylbenzoyl chloridedissolved in 5 ml of dichloromethane, while stirring under ice cooling.After stirring at room temperature for 6 hours, the reaction mixture waswashed with water and then concentrated to give a residue. The residuewas subjected to silica gel chromatography, which afforded 0.25 g of3,5-dichloro-4-(3-(4-trifluoromethylbenzamido)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene(79% yield), m.p., 93.5° C.

PRODUCTION EXAMPLE 3

Production of Compound (10) by Production Process F

To a solution of 0.15 g of 4-trifluoromethylcinnamic acid and 0.07 g oftriethylamine dissolved in 5 ml of dichloromethane was added 0.14 g of1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (WSC) hydrochloride, whilestirring under ice cooling. After stirring for 30 minutes, a solution of0.20 g of3,5-dichloro-4-(2-aminoethoxy)-1-(3,3-dichloro-2-propenyloxy)benzenedissolved in 5 ml of dichloromethane was added dropwise. After stirringat room temperature for 12 hours, the reaction mixture was concentratedto give a residue. The residue was subjected to silica gelchromatography, which afforded 0.20 g of3,5-dichloro-4-(2-(4-trifluoromethylcinnarnamido)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene(63% yield), m.p., 109.4° C.

PRODUCTION EXAMPLE 4

Production of Compound (24) by Production Process G

To a solution of 0.26 g of4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyric acid and0.07 g of triethylamine dissolved in 5 ml of dichloromethane was addeddropwise 0.14 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (WSC)hydrochloride, while stirring under ice cooling. After stirring for 30minutes, a solution of 0.12 g of 4-trifluoromethoxyaniline dissolved in5 ml of dichloromethane was added dropwise. After stirring at roomtemperature for 12 hours, the reaction mixture was concentrated to givea residue. The residue was subjected to silica gel chromatography, whichafforded 0.26 g of3,5-dichloro-4-(3-(N-(4-trifluoromethoxyphenyl)carbamoyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene(70% yield), m.p., 88.8° C.

PRODUCTION EXAMPLE 5

Production of Compound (25) by Production Process I

To a solution of 0.20 g of3,5-dichloro-4-(2-aminoethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene and0.10 g of triethylamine dissolved in 5 ml of dichloromethane was addeddropwise a solution of 0.16 g of 4-trifluoromethoxybenzenesulfonylchloride dissolved in 5 ml of dichloromethane, while stirring under icecooling. After stirring at room temperature for 6 hours, the reactionmixture was concentrated to give a residue. The residue was subjected tosilica gel chromatography, which afforded 0.20 g of3,5-dichloro-4-(2-(4-trifluoromethoxybenzenesulfonamido)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene(60% yield), n_(D) ²³.0 1.5470.

PRODUCTION EXAMPLE 6

Production of Compound (26) by Production Process M

A solution of 0.20 g of3,5-dichloro-4-(2-aminoethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene and0.14 g of 4-trifluoromethoxyphenyl isocyanate dissolved in 10 ml oftoluene was heated under reflux, while stirring, for 12 hours, and thereaction mixture was then concentrated to give a residue. The residuewas subjected to silica gel chromatography, which afforded 0.15 g of3,5-dichloro-4-(2-(N'-(4-trifluoromethoxyphenyl)ureido)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene(46% yield), m.p., 125.4° C.

PRODUCTION EXAMPLE 7

Production of Compound (28) by Production Process K

A solution of 0.17 g of3,5-dichloro-4-(3-hydroxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene,0.09 g of 4-chlorophenyl isocyanate and a catalytic amount of pyridinedissolved in 10 ml of toluene was heated at 60° to 70° C., whilestirring, for 3 hours, and the reaction mixture was then concentrated togive a residue. The residue was subjected to silica gel chromatography,which afforded 0.19 g of3,5-dichloro-4-(3-(N-(4-chlorophenyl)carbamoyloxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene(77% yield), m.p., 54.3° C.

PRODUCTION EXAMPLE 8

Production of Compound (7) by Production Process A

To a mixture of 2.0 g of3,5-dichloro-4-(3-(4-trifluoromethyl)benzamido)propyloxy)phenol, 0.68 gof potassium carbonate and 20 ml of N,N-dimethylformamide was addeddropwise a mixed solution of 0.71 g of 1,1,3-trichloropropene and 5 mlof N,N-dimethylformamide, while stirring at room temperature. Afterstirring at room temperature for 6 hours, the reaction mixture waspoured into ice water and extracted twice with 50 ml of diethyl ether.The ether layers were combined, washed with water, dried over anhydrousmagnesium sulfate, and then concentrated to give crude crystals. Thesecrude crystals were ground and washed with n-hexane, which afforded 1.9g of3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-(trifluoromethyl)benzamido)propyloxy)benzene(75% yield), m.p., 93.5° C.

PRODUCTION EXAMPLE 9

Production of Compound (59) by Production Process A

To a mixture of 0.66 g of3-ethyl-5-methyl-4-(3-(4-(trifluoromethyl)benzamido)propyloxy)phenol,0.29 g of potassium carbonate and 20 ml of N,N-dimethylformamide wasadded dropwise a mixed solution of 0.28 g of 1,1,3-trichloropropene and5 ml of N,N-dimethylformamide, while stirring at room temperature. Afterstirring at room temperature for 6 hours, the reaction mixture waspoured into ice water and extracted twice with 50 ml of diethyl ether.The ether layers were combined, washed with water, dried over anhydrousmagnesium sulfate, and then concentrated to give crude crystals. Thecrude crystals were ground and washed with n-hexane, which afforded 0.48g of3-ethyl-5-methyl-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-(trifluoromethyl)benzamido)propyloxy)benzene(58% yield), m.p., 92.2° C.

PRODUCTION EXAMPLE 10

Production of Compound (67) by Production Process F

To a mixture of 0.96 g of4-(3-aminopropyloxy)-3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)benzene,0.53 g of 5-(trifluoromethyl)-2-pyridinecarboxylic acid, 0.37 g oftriethylamine and 10 ml of chloroform was added 0.64 g of WSChydrochloride, while stirring at room temperature. After stirring atroom temperature for 6 hours, the reaction mixture was concentrated togive a residue. The residue was subjected to silica gel chromatography,which afforded 0.15 g of3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(5-(trifluoromethyl)picolinamido)propoxy)benzene(10% yield), m.p., 55.1° C.

PRODUCTION EXAMPLE 11

Production of Compound (34) by Production Process F

To a mixture of 0.35 g of4-(3-aminopropyloxy)-3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)benzene,0.19 g of 5-bromo-2-furancarboxylic acid, 0.18 ml of triethylamine and10 ml of chloroform was added 0.23 g of WSC hydrochloride, whilestirring at room temperature. After stirring at room temperature for 6hours, the reaction mixture was concentrated to give a residue. Theresidue was dissolved in 50 ml of ethyl acetate, and the ethyl acetatelayer was successively washed with 10% hydrochloric acid, saturatedaqueous sodium hydrogen carbonate solution and saturated salinesolution, dried over anhydrous magnesium sulfate, and then concentratedto give a residue. The residue was subjected to silica gelchromatography, which afforded 0.35 g of3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(5-bromo-2-furancarboxamido)propyloxy)benzene (64% yield), n_(D) ²⁴.0 1.5918.

PRODUCTION EXAMPLE 12

Production of Compound (93) by Production Process F

To a mixture of 0.42 g of3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(methylamino)propyloxy)benzene,0.18 ml of triethylamnine and 10 ml of chloroform was added 0.18 ml of4-(trifluoromethyl)benzoyl chloride, while stirring under ice cooling.After stirring at room temperature for 6 hours, the reaction mixture wasconcentrated to give a residue. The residue was dissolved in 50 ml ofethyl acetate, and the ethyl acetate layer was successively washed with10% hydrochloric acid, saturated aqueous sodium hydrogen carbonatesolution and saturated saline solution, dried over anhydrous magnesiumsulfate, and then concentrated to give a residue. The residue wassubjected to silica gel chromatography, which afforded 0.35 g of3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(N-methyl-4-(trifluoromethyl)benzamido)propyloxy)benzene(55% yield), n_(D) ²⁴.5 1.5461.

PRODUCTION EXAMPLE 13

Production of Compound (100) by Production Process F

To a mixture of 0.35 g of4-(3-aminopropyloxy)-3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)benzene,0.17 g of 4-chlorophenylacetic acid, 0.18 ml of triethylamine and 10 mlof dichloromethane was added 0.23 g of WSC hydrochloride, while stirringat room temperature. After stirring at room temperature for 6 hours, thereaction mixture was concentrated to give a residue. The residue wasdissolved in 50 ml of ethyl acetate, and the ethyl acetate layer wassuccessively washed with 10% hydrochloric acid, saturated aqueous sodiumhydrogen carbonate solution and saturated saline solution, dried overanhydrous magnesium sulfate, and then concentrated to give a residue.The residue was subjected to silica gel chromatography, which afforded0.35 g of3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-chlorophenylacetamido)propyloxy)benzene(70% yield), m.p., 108.4° C.

PRODUCTION EXAMPLE 14

Production of Compound (127) by Production Process F

To a solution of 0.20 g of5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)valeric acid and0.05 g of dipropargylamine dissolved in 10 ml of chloroform was added0.11 g of WSC hydrochloride, while stirring at room temperature. Afterstirring at room temperature for 24 hours, the reaction mixture wasconcentrated to give a residue. The residue was subjected to silica gelchromatography, which afforded 0.21 g of3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(N,N-dipropargylcarbamoyl)butyloxy)benzene(92% yield), n_(D) ²⁵.0 1.5481.

PRODUCTION EXAMPLE 15

Production of Compound (129) by Production Process L

A mixture of 0.33 g of3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(aminopropyloxy)benzeneand 10 ml of pyridine was cooled to 0° C., and 0.10 g of methylchloroformate was slowly added dropwise, while stirring. The reactionmixture was stirred at 0° C. for 1 hours, after which the temperaturewas slowly raised to room temperature, and the reaction mixture wasfurther stirred at room temperature for 6 hours. The reaction mixturewas poured into 10% hydrochloric acid, and the mixture was extractedtwice with 50 ml of ethyl acetate. The ethyl acetate layers werecombined, washed with water, dried over anhydrous magnesium sulfate, andthen concentrated, which afforded 0.30 g of3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-methoxycarbonylarnino)propyloxy)benzene(74% yield), n_(D) ²⁵¹.5 1.5421.

The following are specific examples of the present compounds with theircompound numbers and physical properties, if measured.

(1)3,5-Dichloro-4-(3-benzamidopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzenen_(D) ²³.0 1.5860

(2)3,5-Dichloro-4-(3-(4-chlorobenzamido)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 95.1° C.

(3)3,5-Dichloro-4-(2-(4-trifluoromethoxybenzamido)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 81.0° C.

(4)3,5-Dichloro-4-(3-(4-trifluoromethoxybenzamido)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 93.8° C.

(5)3,5-Dichloro-4-(3-(4-fluorobenzamido)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzenen_(D) ²⁴.5 1.5800

(6)3,5-Dichloro-4-(3-(4-bromobenzamido)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 102.7° C.

(7)3,5-Dichloro-4-(3-(4-trifluoromethylbenzamiddo)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 93.5° C.

(8)3,5-Dichloro-4-(3-(4-ethoxybenzamido)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 120.6° C.

(9)3,5-Dichloro-4-(3-(4-isopropoxybenzamido)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 91.8° C.

(10)3,5-Dichloro-4-(2-(4-trifluoromethylcinnamamido)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 109.4° C.

(11)3,5-Dichloro-4-(3-(4-trifluoromethylcinnamamido)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 116.6° C.

(12) 3,5-Dichloro-4-(3-(2-chlorobenzamido)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 70.3° C.

(13)3,5-Dichloro-4-(3-(3-chlorobenzamido)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 70.3° C.

(14)3,5-Dichloro-4-(3-(2,4-dichlorobenzamido)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 118.5° C.

(15)3,5-Dichloro-4-(3-(2,6-dichlorobenzamido)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 124.6° C.

(16)3,5-Dichloro-4-(3-(2,4,6-trichlorobenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 126.1° C.

(17)3,5-Dichloro-4-(3-(2-trifluoromethylbenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 98.9° C.

(18)3,5-Dichloro-4-(3-(3-trifluoromethylbenzamido)propoxy)-(1-(3,3-dichloro-2-propenyloxy)benzenem.p., 73.5° C.

(19)3,5-Dichloro-4-(3-(3,5-bistrifluoromethylbenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 110.4° C.

(20)3,5-Dichloro-4-(3-(4-tert-butylbenzamido)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 109.5° C.

(21)3,5-Dichloro-4-(3-(3,4-dichlorobenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 85.9° C.

(22)3,5-Dichloro-4-(3-(4-nitrobenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 136.0° C.

(23)3,5-Dichloro-4-(3-(4-cyanobenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 111.7° C.

(24)3,5-Dichloro-4-(3-(N-(4-trifluoromethoxyphenyl)carbamoyl)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 88.8° C.

(25)3,5-Dichloro-4-(2-(4-trifluoromethoxybenzenesulfonamido)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzenen_(D) ²³.0 1.5470

(26)3,5-Dichloro-4-(2-(N'-(4-trifluoromethoxyphenyl)ureido)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 125.4° C.

(27)3,5-Dichloro-4-(3-(N-phenylcarbamoyloxy)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzenen_(D) ²⁴.5 1.5777

(28)3,5-Dichloro-4-(3-(N-(4-chlorophenyl)carbamoyloxy)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 54.3° C.

(29)3,5-Dichloro-4-(2-(N-(4-chlorophenyl)carbamoyloxy)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 105.5° C.

(30)3,5-Dichloro-4-(2-(N-(4-trifluoromethoxyphenyl)carbamoyloxy)-ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzenen_(D) ²⁴.5 1.5446

(31)3,5-Dichloro-4-(3-(6-chloronicotinamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 85.6° C.

(32)3,5-Dichloro-4-(4-(4-trifluoromethylbenzamido)butoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 90.5° C.

(33)3,5-Dichloro-4-(3-(thiophene-2-carboxamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzenen_(D) ²⁴.0 1.6026

(34)3,5-Dichloro-4-(3-(5-bromofurane-2-carboxamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzenen_(D) ²⁴.0 1.5918

(35)3,5-Dichloro-4-(3-(5-chloroindole-2-carboxamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 153.9° C.

(36)3,5-Dichloro-4-(3-(4-chrorobenzamido)propoxy)-1-(3,3-dibromo-2-propenyloxy)benzene

(37)3,5-Dibromo-4-(3-(4-chlorobenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(38)3,5-Dimethyl-4-(3-(4-chlorobenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(39)3,5-Diethyl-4-(3-(4-chlorobenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(40)3-Chloro-5-fluoro-4-(3-(4-chlorobenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(41)3-Chloro-5-methyl-4-(3-(4-chlorobenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(42)3-Chloro-5-ethyl-4-(3-(4-chlorobenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(43)3-Ethyl-5-methyl-4-(3-(4-chlorobenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(44)3,5-Dichloro-4-(4-(4-chlorobenzamido)butoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 96.5° C.

(45)3,5-Dichloro-4-(4-(4-chlorobenzamido)butoxy)-1-(3,3-dibromo-2-propenyloxy)benzene

(46)3,5-Dibromo-4-(4-(4-chlorobenzamido)butoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(47)3,5-Dimethyl-4-(4-(4-chlorobenzamido)butoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(48)3,5-Diethyl-4-(4-(4-chlorobenzamido)butoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(49)3-Chloro-5-fluoro-4-(4-(4-chlorobenzamido)butoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(50)3-Chloro-5-methyl-4-(4-(4-chlorobenzamido)butoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(51)3-Chloro-5-ethyl-4-(4-(4-chlorobenzamido)butoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(52)3-Ethyl-5-methyl-4-(4-(4-chlorobenzamido)butoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(53)3,5-Dichloro-4-(3-(4-trifluoromethylbenzamido)propoxy)-1-(3,3-dibromo-2-propenyloxy)benzene

(54)3,5-Dibromo-4-(3-(4-trifluoromethylbenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(55)3,5-Dimethyl-4-(3-(4-trifluoromethylbenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(56)3,5-Diethyl-4-(3-(4-trifluoromethylbenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 99.5° C.

(57)3-Chloro-5-fluoro-4-(3-(4-trifluoromethylbenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(58)3-Chloro-5-methyl-4-(3-(4-trifluoromethylbenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 91.0° C.

(59)3-Ethyl-5-methyl-4-(3-(4-trifluoromethylbenzamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 92.2° C.

(60)3,5-Dichloro-4-(4-(4-trifluoromethylbenzamido)butoxy)-1-(3,3-dibromo-2-propenyloxy)benzene

(61)3,5-Dibromo-4-(4-(4-trifluoromethylbenzamido)butoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(62)3,5-Dimethyl-4-(4-(4-trifluoromethylbenzamido)butoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(63)3,5-Diethyl-4-(4-(4-trifluoromethylbenzamido)butoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(64)3-Chloro-5-fluoro-4-(4-(4-trifluoromethylbenzamido)butoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(65)3-Chloro-5-methyl-4-(4-(4-trifluoromethylbenzamido)butoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(66)3-Ethyl-5-methyl-4-(4-(4-trifluoromethylbenzamido)butoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(67)3,5-Dichloro-4-(3-(5-trifluoromethylpicolinamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzenem.p., 55.1° C.

(68)3,5-Dichloro-4-(3-(5-trifluoromethylpicolinamido)propoxy)-1-(3,3-dibromo-2-propenyloxy)benzene

(69)3,5-Dibromo-4-(3-(5-trifluoromethylpicolinamnido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(70)3,5-Dimethyl-4-(3-(5-trifluoromethylpicolinamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(71)3,5-Diethyl-4-(3-(5-trifluoromethylpicolinamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(72)3-Chloro-5-fluoro-4-(3-(5-trifluoromethylpicolinamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(73)3-Chloro-5-methyl-4-(3-(5-trifluoromethylpicolinamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(74) 3-Ethyl-5-methyl-4-(3-(5-trifluoromethylpicolinamido)propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(75)3,5-Dichloro-4-(4-(5-trifluoromethylpicolinamido)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(76)3,5-Dichloro-4-(4-(5-trifluoromethylpicolinamido)butyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

(77)3,5-Dibromo-4-(4-(5-trifluoromethylpicolinamido)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(78)3,5-Dimethyl-4-(4-(5-trifluoromethylpicolinamido)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(79)3,5-Diethyl-4-(4-(5-trifluoromethylpicolinamido)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(80)3-Chloro-5-fluoro-4-(4-(5-trifluoromethylpicolinamido)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(81)3-Chloro-5-methyl-4-(4-(5-trifluoromethylpicolinamido)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(82)3-Ethyl-5-methyl-4-(4-(5-trifluoromethylpicolinamido)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(83)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(5-methyl-1,4-benzodioxane-6-carboxamido)propoxy)benzenem.p., 120.8° C.

(84)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(2-pyrazinecarboxamido)propoxy)benzenen_(D) ²⁸.0 1.5825

(85)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-pyridazinecarboxamido)propoxy)benzeneglassy

(86) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(1-methyl-2-indolecarboxamido)propoxy)benzene m.p., 123.3° C.

(87)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(6,6-dimethyl-5,6-dihydro-4H-pyran-4-one-2-carboxamido)propoxy)benzenen_(D) ²⁸.0 1.5612

(88)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-oxo-4H-1-benzopyrane-2-carboxamido)propoxy)benzenem.p., 165.7° C.

(89)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(1-methyl-2-pyrrolecarboxamido)propoxy)benzenen_(D) ²⁸.0 1.5772

(90)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(2-quinolinecarboxamido)propoxy)benzenem.p., 145.8° C.

(91)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(5-methyl-2-pyrazinecarboxamido)propoxy)benzenem.p., 109.0° C.

(92)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(N-methyl-4-(trifluoromethyl)benzamido)butoxy)benzenen_(D) ²⁶.0 1.5417

(93)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(N-methyl-4-(trifluoromethyl)benzamido)propoxy)benzenen_(D) ²⁴.5 1.5461

(94)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(2-furancarboxamido)propoxy)benzenen_(D) ²⁴.5 1.5682

(95)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(3-furancarboxamido)propoxy)benzenen_(D) ²⁴.5 1.5695

(96)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(3-thiophenecarboxamido)propoxy)benzenen_(D) ²⁴.5 1.5824

(97)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(5-methylthiophenecarboxamido)propoxy)benzenem.p., 85.4° C.

(98)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-propylbenzamido)propoxy)benzenem.p., 92.9° C.

(99)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(6-methyl-3-pyridinecarboxamido)propoxy)benzenem.p., 94.8° C.

(100) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-chlorophenylacetamido)propoxy)benzene m.p., 108.4° C.

(101)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(3-(trifluoromethyl)-phenylacetamido)propoxy)benzenem.p., 88.7° C.

(102)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(N-isopropyl-4-(trifluoromethyl)benzamido)butoxy)benzenen_(D) ²⁴.5 1.5394

(103)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(N-(4-(trifluoromethyl)phenyl)carbamoyl)propoxy)benzenem.p., 112.8° C.

(104)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(N-(4-(trifluoromethyl)phenyl)carbamoyl)butoxy)benzenem.p., 111.5° C.

(105)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(1-methyl-5-nitro-4-pyrazolecarboxamido)propoxy)benzenem.p., 122.2° C.

(106)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(3-quinolinecarboxamido)propoxy)benzenem.p., 115.9° C.

(107)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(5-nitro-2-furancarboxamido)propoxy)benzenen_(D) ²¹.0 1.5850

(108)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(5-(trifluoromethyl)-2-pyridinecarboxamido)propoxy)benzenem.p., 66.8° C.

(109)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(N-(5-bromo-2-thiazole)carbamoyl)propoxy)benzenem.p., 164.0° C.

(110)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(4-chlorobenzenesulfonamido)butoxybenzenen_(D) ²¹.5 1.5745

(111)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(5-bromo-2-furancarboxamido)butoxybenzenen_(D) ²¹.5 1.5801

(112)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(5-methyl-2-thiophenecarboxamido)butoxybenzenem.p., 105.2° C.

(113)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3-quinolinecarboxamido)butoxybenzenem.p., 110.1° C.

(114)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(dipropylcarbamoyl)butoxy)benzenen_(D) ²⁶.5 1.5291

(115)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(5-(dipropylcarbamoyl)pentoxy)benzenen_(D) ²⁴.0 1.5271

(116) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(diethylcarbamoyl)butoxy)benzene n_(D) ²⁵.0 1.5386

(117)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(trifluoroacetamido)propoxy)benzenem.p., 68.1° C.

(118)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(trifluoromethanesulfonyl)propoxy)benzenem.p., 47.2° C.

(119)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(acetamidopropoxy)benzenem.p., 77.8° C.

(120)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(1-piperidylcarbonyl)butoxy)benzenen_(D) ²⁴.5 1.5423

(121)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(1-pyrrolidinylcarbonyl)butoxy)benzenen_(D) ²⁴.5 1.5537

(122)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(2-(1-piperidylcarbonyl)ethoxy)benzenen_(D) ²¹.0 1.5517

(123)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(1-piperidylcarbonyl)propoxy)benzenen_(D) ²⁵.0 1.5510

(124)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(N,N-diallylcarbamoyl)butoxy)benzenen_(D) ²⁶.5 1.5432

(125)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(5-(1-piperidylcarbonyl)pentoxy)benzenen_(D) ²⁴.0 1.5395

(126)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(5-(N,N-diallylcarbamoyl)pentoxy)benzenen_(D) ²⁴.0 1.5396

(127)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(N,N-dipropargylcarbamoyl)butoxy)benzenen_(D) ²⁵.0 1.5481

(128)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(4-morpholinylcarbonyl)butoxy)benzenen_(D) ²⁵.5 1.5450

(129) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(methoxycarbonylamino)propoxy)benzene n_(D) ²⁵.5 1.5421

(130) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(methoxycarbonylamino)butoxy)benzene n_(D) ²⁴.5 1.5440

(131)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(ethoxycarbonylamino)butoxy)benzenen_(D) ²⁴.5 1.5375

(132)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(propyloxycarbonylamino)butoxy)benzenen_(D) ²⁴.5 1.5339

(133)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(tert-butyramidopropoxy)benzenen_(D) ²³.0 1.5407

(134) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(2,4-bis(trifluoromethyl)benzamido)propoxy)benzene

(135) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(2,4-bis(trifluoromethyl)benzamido)butyroxy)benzene

(136)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(2-fluoro-4-(trifluoromethyl)benzamido)propoxy)benzene

(137)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(2-fluoro-4-(trifluoromethyl)benzamido)butyroxy)benzene

(138)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(2-nitro-4-(trifluoromethyl)benzamido)propoxy)benzene

(139)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(2-nitro-4-(trifluoromethyl)benzamido)butyroxy)benzene

(140)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-chloro-2-fluorobenzamido)propoxy)benzene

(141)3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(4-chloro-2-fluorobenzamido)butyroxy)benzene

(142)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(2-chloro-5-(trifluoromethyl)benzamido)propoxy)benzene

(143)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(2-chloro-5-(trifluoromethyl)benzamido)butyroxy)benzene

(144)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(2,5-dichlorobenzamido)propoxy)benzene

(145)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(2,5-dichlorobenzamido)butyroxy)benzene

(146)3,5-Diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(3-(2,4-bis(trifluoromethyl)benzamido)propoxy)benzene

(147)3,5-Diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(3-(2-fluoro-4-(trifluoromethyl)benzamido)propoxy)benzene

(148)3,5-Diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-chloro-2-fluorobenzamido)propoxy)benzene

The following are production examples for the intermediates of generalformula [IX].

Intermediate Production Example 1

Production of Intermediate Compound 1)

A reaction vessel was charged with 30.5 g of 4-hydroxyphenyl benzoate,21.6 g of potassium carbonate, 20.8 g of 1,1,3-trichloropropene and 100ml of N,N-dimethylformamide. After stirring at room temperature for 15hours, the reaction mixture was poured into water and extracted twicewith 150 ml of diethyl ether. The ether layers were combined, washedwith water, dried over anhydrous magnesium sulfate, and thenconcentrated to give a crude product. The crude product was subjected tosilica gel chromatography, which afforded 44.1 g of4-(3,3-dichloro-2-propenyloxy)phenyl benzoate (96% yield).

A reaction vessel was charged with 44.1 g of4-(3,3-dichloro-2-propenyloxy)phenyl benzoate and 400 ml of methanol,and 33 g of 30% aqueous potassium hydroxide solution was slowly addeddropwise under ice cooling. After stirring for 1 hour, the mixture wasmade weak acidic by the addition of 10% hydrochloric acid, and thenextracted twice with 150 m of diethyl ether under salting out. The etherlayers were combined, washed with water, dried over anhydrous magnesiumsulfate, and then concentrated to give a crude product. The crudeproduct was subjected to silica gel chromatography, which afforded 26.0g of 4-(3,3-dichloro-2-propenyloxy)phenol (87% yield).

A reaction vessel was charged with 26.0 g of4-(3,3-dichloro-2-propenyloxy)phenol and 500 ml of carbon tetrachloride,and a solution of 27.1 g of t-butyl hypochlorite dissolved in 20 ml ofcarbon tetrachloride was slowly added dropwise, while stirring undercooling. After stirring for 24 hours, the reaction mixture was pouredinto water, and the organic layer (carbon tetrachloride layer) wasseparated. The organic layer was washed with water, dried over anhydrousmagnesium sulfate, and then concentrated to give a crude product. Thecrude product was subjected to silica gel chromatography, which afforded11.0 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol (32% yield),n_(D) ²².5 1.5895.

The following are some specific examples of the intermediates of generalformula [IX] with their compound numbers and physical properties, ifmeasured.

1) 2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenol

¹ H-NMR (CDCl₃ /TMS) δ (ppm): 4.57 (2H, d), 5.50 (1H, brs), 6.11 (1H,t), 6.85 (2H, s)

2) 2,6-Dichloro-4-(3,3-dibromo-2-propenyloxy)phenol

3) 2-Chloro-6-bromo-4-(3,3-dichloro-2-propenyloxy)phenol

4) 2-Chloro-6-bromo-4-(3,3-dibromo-2-propenyloxy)phenol

5) 2,6-Dibromo-4-(3,3-dichloro-2-propenyloxy)phenol

6) 2,6-Dibromo-4-(3,3-dibromo-2-propenyloxy)phenol

7) 2,6-Dimethyl-4-(3,3-dichloro-2-propenyloxy)phenol

8) 2,6-Dimethyl-4-(3,3-dibromo-2-propenyloxy)phenol

9) 2-Chloro-6-methyl-4-(3,3-dichloro-2-propenyloxy)phenol

10) 2-Chloro-6-methyl-4-(3,3-dibromo-2-propenyloxy)phenol

The following are production examples for the intermediates of generalformula [XVIII].

Intermediate Production Example 2

Production of Intermediate Compound 12)

A reaction vessel was charged with 10.6 g of 1,3-dibromopropane, 5.53 gof potassium carbonate and 100 ml of N,N-dimethylformamide, and asolution of 10.1 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoldissolved in 40 ml of N,N-dimethylformamide was slowly added dropwise.After stirring at room temperature for 24 hours, the reaction mixturewas poured into water and extracted twice with 150 ml of diethyl ether.The ether layers were combined, washed with water, dried over anhydrousmagnesium sulfate, and then concentrated to give a crude product. Thecrude product was subjected to silica gel chromatography, which afforded11.1 g of3,5-dichloro-4-(3-bromopropoxy)-1-(3,3-dichloro-2-propenyloxy)benzene(77% yield).

A reaction vessel was charged with 11.1 g of3,5-dichloro-4-(3-bromopropoxy)-1-(3,3-dichloro-2-propenyloxy)benzene,3.31 g of benzoic acid, 3.90 g of potassium carbonate and 50 ml ofN,N-dimethylformamide. After stirring at room temperature for 24 hours,the reaction mixture was poured into water and extracted twice with 150ml of diethyl ether. The ether layers were combined, and washed withwater, dried over anhydrous magnesium chloride, and then concentrated togive a crude product. The crude product was subjected to silica gelchromatography, which afforded 11.6 g of3,5-dichloro-4-(3-benzoyloxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene(95% yield).

A reaction vessel was charged with 11.6 g of3,5-dichloro-4-(3-benzoyloxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene,15.2 g of 10% aqueous potassium hydroxide solution and 30 ml ofmethanol. After stirring at room temperature for 24 hours, the reactionmixture was concentrated. Water was poured into the concentrate, and themixture was extracted twice with 150 ml of diethyl ether. The etherlayers were combined, washed with water, dried over anhydrous magnesiumsulfate, and then concentrated to give a crude product. The crudeproduct was subjected to silica gel chromatography, which afforded 7.41g of 3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-1-propanol(83% yield), m.p., 56.6° C.

The following are some specific examples of the intermediates of generalformula [XVIII] with their compound numbers and physical properties, ifmeasured.

11) 2-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethanol

12) 3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-1-propanolm.p., 56.6° C.

13) 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-1-butanol

14) 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-1-pentanol

15) 2-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-1-ethanethiol

16)3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-1-propanethiol

17) 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-1-butanethiol

18)5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-1-pentanethiol

The following are production examples for the intermediates of generalformula [III] or [XII].

Intermediate Production Example 3

Production of Intermediate Compound 21)

A reaction vessel was charged with 4.09 g of3,5-dichloro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene,2.41 of potassium phthalimide and 30 ml of N,N-dimethylformamide. Afterstirring at room temperature for 24 hours, the reaction mixture waspoured into water and extracted twice with 150 ml of chloroform. Thechloroform layers were combined, washed with diluted hydrochloric acidand diluted aqueous sodium hydroxide, dried over anhydrous magnesiumsulfate, and then concentrated, which afforded 4.67 g of crude3,5-dichloro-4-(3-phthalimidopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene(98% yield).

A reaction vessel was charged with 4.67 g of crude3,5-dichloro-4-(3-phthalimidopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene,0.55 g of hydrazine monohydrate and 200 ml of ethanol. After heatingunder reflux for 2 hours, the reaction mixture was made weak acidic bythe addition of concentrated hydrochloric acid, and then further heatedunder reflux for 1 hours. The deposited solid was collected byfiltration, and the filtrate was concentrated. Water was poured into theconcentrated, and the mixture was extracted twice with 150 ml ofchloroform. The chloroform layers were combined, washed with water,dried over anhydrous magnesium sulfate, and then concentrated to give acrude product. The crude product was subjected to silica gelchromatography which afforded 2.4 of3,5-dichloro-4-(3-aminopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene(71% yield), n_(D) ²³.5 1.5672.

Intermediate Production Example 4

Production of Intermediate Compound 23)

A mixture of 9.1 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol,8.9 g of N-(4-bromoethyl)phthalimide, 4.4 g of potassium carbonate and100 ml of N,N-dimethylformamide was stirred at room temperature for 24hours. The reaction mixture was poured into ice water and made weakacidic by the addition of 10% hydrochloric acid, after which 200 ml ofethyl acetate was added for extraction. The ethyl acetate layer wassuccessively washed with 10% hydrochloric acid and saturated salinesolution, dried over anhydrous magnesium sulfate, and then concentratedto give crude crystals. The crude crystals were washed with n-hexane andthen dried under reduced pressure, which afforded 14.5 g of3,5-dichloro-4-(4-phthalimidobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene(94% yield).

A mixture of 14.5 g of3,5-dichloro-4-(4-phthalimidobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene,1.73 ml of hydrazine monohydrate and 100 ml of ethanol was heated underreflux for 4 hours. The reaction mixture was made weak acidic by theaddition of concentrated hydrochloric acid and further heated underreflux for 1 hour. The temperature of the reaction mixture was decreasedto room temperature, after which the deposited solid was collected byfiltration and the filtrate was concentrated to give a residue. To theresidue was added a solution of 2.1 g of potassium hydroxide dissolvedin 100 ml of ethanol, after which the deposited solid was collected byfiltration and the filtrate was concentrated to give a residue. To theresidue was added 100 ml of diethyl ether for dissolution, and thesolution was dried over anhydrous magnesium sulfate and thenconcentrated, which afforded 7.51 g of3,5-dichloro-4-(4-aminobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene(71% yield), n_(D) ²³.5 1.5672.

Intermediate Production Example 5

Production of Intermediate Compound 60)

A mixture of 1.0 g of3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-bromobutyloxy)benzene,4 ml of 40% methanol solution of methylamine, 0.33 g of potassiumcarbonate and N,N-dimethylformamide was stirred at room temperature for24 hours. To the reaction mixture was added 100 ml of saturated aqueoussodium hydrogen carbonate solution, and the mixture was extracted with100 ml of ethyl acetate. The ethyl acetate layer was successively washedwith 100 ml of saturated sodium hydrogen carbonate and saturated salinesolution, dried over anhydrous magnesium sulfate, and then concentrated,which afforded 0.80 g of3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(methylamino)butyloxy)benzene(89% yield), n_(D) ²⁶.0 1.5545.

The following are some specific examples of the intermediates of generalformula [III] or [XII] with their compound numbers and physicalproperties, if measured.

19) 3,5-Dichloro-4-(2-aminoethoxy)-1-(3,3-dichloro-2-propenyloxy)benzenen_(D) ²⁵.0 1.5784

20) 3,5-Dichloro-4-(2-aminoethoxy)-1-(3,3-dibromo-2-propenyloxy)benzene

21)3,5-Dichloro-4-(3-aminopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzenen_(D) ²³.5 1.5672

22)3,5-Dichloro-4-(3-aminopropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

23)3,5-Dichloro-4-(4-aminobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzenen_(D) ²⁴.5 1.5722

24)3,5-Dichloro-4-(4-aminobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

25)3,5-Dichloro-4-(5-aminopentyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

26)3,5-Dichloro-4-(5-aminopentyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

27) 3,5-Dibromo-4-(2-aminoethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

28) 3,5-Dibromo-4-(2-aminoethoxy)-1-(3,3-dibromo-2-propenyloxy)benzene

29)3,5-Dibromo-4-(3-aminopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

30)3,5-Dibromo-4-(3-aminopropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

31)3,5-Dibromo-4-(4-aminobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

32) 3,5-Dibromo-4-(4aminobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

33)3,5-Dibromo-4-(5-aminopentyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

34)3,5-Dibromo-4-(5-aminopentyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

35) 3,5-Dimethyl-4-(2-aminoethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

36) 3,5-Dimethyl-4-(2-aminoethoxy)-1-(3,3-dibromo-2-propenyloxy)benzene

37)3,5-Dimethyl-4-(3-aminopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

38)3,5-Dimethyl-4-(3-aminopropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

39)3,5-Dimethyl-4-(4aminobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

40)3,5-Dimethyl-4-(4-aminobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

41)3,5-Dimethyl-4-(5-aminopentyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

42)3,5-Dimethyl-4-(5-aminopentyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

43)3-Chloro-5-methyl-4-(2-aminoethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

44)3-Chloro-5-methyl-4-(2-aminoethoxy)-1-(3,3-dibromo-2-propenyloxy)benzene

45)3-Chloro-5-methyl-4-(3-aminopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

46)3-Chloro-5-methyl-4-(3-aminopropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzen

47)3-Chloro-5-methyl-4-(4-aminobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

48)3-Chloro-5-methyl-4-(4-aminobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

49)3-Chloro-5-methyl-4-(5-aminopentyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

50)3-Chloro-5-methyl-4-(5-aminopentyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

51)3-Ethyl-5-methyl-4-(2-aminoethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

52) 3-Ethyl-5-methyl -4-(2-aminoethoxy)-1-(3,3-dibromo-2-propenyloxy)benzene

53)3-Ethyl-5-methyl-4-(3-aminopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

54)3-Ethyl-5-methyl-4-(3-aminopropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

55)3-Ethyl-5-methyl-4-(4-aminobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

56)3-Ethyl-5-methyl-4-(4-aminobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

57) 3-Ethyl-5-methyl-4-(5-aminopentyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

58)3-Ethyl-5-methyl-4-(5-aminopentyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

59)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(methylamino)propyloxy)benzenen_(D) ²⁶.0 1.5618

60)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(methylamino)butyloxy)benzenen_(D) ²⁶.0 1.5545

61)3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(isopropylamino)butyloxy)benzenen_(D) ²⁴.5 1.5355

The following are production examples for the intermediates of generalformula [III] or [XII].

Intermediate Production Example 6

Production of Intermediate Compound 62)

A reaction vessel was charged with 2.02 g of2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 1.56 g of ethyl3-bromobutyrate, 1.11 g of potassium carbonate and 20 ml ofN,N-dimethylformamide. After stirring at room temperature for 12 hours,the reaction mixture was poured into water and extracted twice with 50ml of diethyl ether. The ether layers were combined, washed with water,dried over anhydrous magnesium sulfate, and then concentrated to give acrude product. The crude product was subjected to silica gelchromatography, which afforded 2.54 g of ethyl2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxybutyrate (90% yield).

A reaction vessel was charged with 2.54 g of ethyl2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxybutyrate, 4.0 g of 10%aqueous potassium hydroxide solution and 50 ml of methanol. Afterstirring at room temperature for 24 hours, the reaction mixture wasconcentrated. Then, 50 ml of diethyl ether was poured into the reactionmixture, and the mixture was extracted twice with 50 ml of 5% aqueoussodium hydrogen carbonate solution. The aqueous layers were combined,and made weak acidic by the addition of concentrated hydrochloric acid.The deposited crystals were extracted twice with 50 ml of diethyl ether.The ether layers were combined, washed with water, dried over anhydrousmagnesium sulfate, and then concentrated, which afforded 2.11 g of4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyric acid (90%yield), m.p., 80.9° C.

The following are some specific examples of the intermediates of generalformula [III] or [XIV] with their compound number and physicalproperties, if measured.

62) 4-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyric acidm.p., 80.9° C.

63) 4-(2,6-Dichloro-4-(3,3-dibromo-2-propenyloxy)phenoxy)butyric acid

64) 5-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)valeric acidm.p., 75.7° C.

65) 5-(2,6-Dichloro-4-(3,3-dibromo-2-propenyloxy)phenoxy)valeric acid

66) 4-(2,6-Dibromo-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyric acid

67) 4-(2,6-Dibromo-4-(3,3-dibromo-2-propenyloxy)phenoxy)butyric acid

68) 5-(2,6-Dibromo-4-(3,3-dichloro-2-propenyloxy)phenoxy)valeric acid

69) 5-(2,6-Dibromo-4-(3,3-dibromo-2-propenyloxy)phenoxy)valeric acid

70) 4-(2,6-Dimethyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyric acid

71) 4-(2,6-Dimethyl-4-(3,3-dibromo-2-propenyloxy)phenoxy)butyric acid

72) 5-(2,6-Dimethyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)valeric acid

73) 5-(2,6-Dimethyl-4-(3,3-dibromo-2-propenyloxy)phenoxy)valeric acid

74) 4-(2-Chloro-6-methyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyricacid

75) 4-(2-Chloro-6-methyl-4-(3,3-dibromo-2-propenyloxy)phenoxy)butyricacid

76) 5-(2-Chloro-6-methyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)valericacid

77) 5-(2-Chloro-6-methyl-4-(3,3-dibromo-2-propenyloxy)phenoxy)valericacid

78) 4-(2-Ethyl-6-methyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyricacid

79) 4-(2-Ethyl-6-methyl-4-(3,3-dibromo-2-propenyloxy)phenoxy)butyricacid

80) 5-(2-Ethyl-6-methyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)valericacid

81) 5-(2-Ethyl-6-methyl-4-(3,3-dibromo-2-propenyloxy)phenoxy)valericacid

The following are production examples for the intermediates of generalformula [IV] or [V].

Intermediate Production Example 7

Production of Intermediate Compound 84)

A reaction vessel was charged with 7.51 g of 3-amino-1-propanol, 2.53 gof triethylamine and 50 ml of dichloromethane, and 5.21 g of4-trifluoromethylbenzoyl chloride was slowly added dropwise under icecooling. After stirring at room temperature for 6 hours, the reactionmixture was successively washed with diluted hydrochloric acid andwater, dried over anhydrous magnesium sulfate, and then concentrated,which afforded 5.25 g of 3-(4-trifluoromethylbenzamido)propan-1-ol (85%yield).

A reaction vessel was charged with 5.25 g (21.2 mmol) of3-(4-(trifluoromethyl)benzamido)propan-1-ol, 5.72 g (21.2 mmol) of4-benzyloxy-2,6-dichlorophenol, 5.29 g (20.2 mmol) of triphenylphosphineand 100 ml of tetrahydrofuran, and a solution of 4.08 g (20.2 mmol) ofdiisopropyl azodicarboxylate dissolved in 20 ml of tetrahydrofuran wasadded dropwise, while stirring. After stirring at room temperature for12 hours, the reaction mixture was concentrated, and the residue wassubjected to silica gel chromatography, which afforded1-benzyloxy-3,5-dichloro-4-(3-(4-trifluoromethylbenzamido)propyloxy)benzene.

1-Benzyloxy-3,5-dichloro-4-(3-(4-trifluoromethylbenzamido)propyloxy)benzenewas dissolved in ethyl acetate, which was put into a reaction vessel,and the air in the vessel was replaced with nitrogen gas. A catalyticamount of 10% palladium on carbon was added, and the nitrogen gas in thevessel was replaced with hydrogen gas, followed by vigorous stirring atroom temperature for 24 hours. The hydrogen gas in the vessel wasreplaced with nitrogen gas, after which the reaction mixture wasfiltered through cerite and the filtrate was concentrated to give3,5-dichloro-4-(3-(4-trifluoromethylbenzamido)propyloxy)phenol.

Intermediate Production Example 8

Production of Intermediate Compound 120)

To a mixture of 27 g of 2-ethyl-6-methylaniline, 36 ml of concentratedsulfuric acid and 100 ml of water was added dropwise a solution of 16.1g of sodium nitrite dissolved in 50 ml of water, while stirring at atemperature of 0° to 5° C. After completion of the dropwise addition,150 g of chilled water, 1.5 g of urea and 150 g of ice were added.

This aqueous solution was added dropwise to a mixture of 100 ml ofsulfuric acid, 100 ml of water and 150 g of sodium sulfate as a solutionwhich was heating at 135° C. under stirring. Upon the dropwise addition,steam distillation was carried out. After completion of the dropwiseaddition, an aqueous solution obtained by the steam distillation wassubjected to salting out with sodium chloride, dried over anhydrousmagnesium sulfate, and then concentrated to give a crude product. Thecrude product was subjected to silica gel chromatography, which afforded16 g of 2-ethyl-6-methylphenol (59% yield).

Then, 16 g of 2-ethyl-6-methylphenol was dissolved in 200 ml ofchloroform, which was stirred at 0° C., and 56.6 g of tetrabutylammoniumtribromide was added in small portions to this solution. After stirringat room temperature for 1 hour, the solvent was distilled out underreduced pressure. The residue was dissolved in 300 ml of diethyl ether,successively washed with 10% hydrochloric acid and water, dried overanhydrous magnesium sulfate, and then concentrated to give a crudeproduct. The crude product was subjected to silica gel chromatography,which afforded 23 g of 4-bromo-2-ethyl-6-methylphenol (92% yield).

To a mixture of 26 g of 4-bromo-2-ethyl-6-methylphenol, 24.8 g of benzylbromide and 200 ml of N,N-dimethylformamide was added 21.7 g ofpotassium carbonate, while stirring at room temperature. After stirringat room temperature for 24 hours, the reaction mixture was poured intoice water, and extracted twice with 500 ml of diethyl ether. The diethylether layers were combined, washed with water, dried over anhydrousmagnesium sulfate, and then concentrated to give a crude product. Thecrude product was subjected to silica gel chromatography, which afforded35.6 g of 4-bromo-2-ethyl-6-methyl-1-benzyloxybenzene (97% yield).

Then, 35.6 g of 4-bromo-2-ethyl-6-methyl-1-benzyloxybenzene wasdissolved in 250 ml of tetrahydrofuran, and 69 ml of n-butyl lithiumsolution (in hexane; 1.69 mol/liter), while stirring at -70° C. Afterfurther stirring at -70° C. for 2 hours, a solution of 12.1 g oftrimethoxyboron dissolved in 50 ml of tetrahydrofuran was added dropwiseto the reaction mixture. After completion of the dropwise addition, thereaction mixture was returned to room temperature, stirred for 1 hour,and then poured into ice water. The mixture was made weak acidic by theaddition of 10% hydrochloric acid, and extracted twice with 500 ml ofdiethyl ether. The ether layers was combined, washed with water, driedover anhydrous magnesium sulfate, and then concentrated to give aresidue. To the residue was added 120 ml of toluene, and 33 ml of 30%aqueous hydrogen peroxide was added dropwise, while heating at 70° C.under stirring. After heating under reflux for 1 hours, the reactionmixture was returned to room temperature, washed once with water, twicewith 10% aqueous ferrous ammonium sulfate and then once with water. Thetoluene layer was dried over anhydrous magnesium sulfate, and thenconcentrated to give a crude product. The crude product was subjected tosilica gel chromatography, which afforded 26.2 g of3-ethyl-4-benzyloxy-5-methylphenol (93% yield).

To a mixture of 6.3 g of 4-benzyloxy-3-ethyl-5-methylphenol, 3.2 g oftriethylamine and 50 ml of chloroform was added dropwise 4.0 g ofbenzoyl chloride, while stirring at 0° C. After stirring at roomtemperature for 6 hours, the reaction mixture was concentrated underreduced pressure to give a residue. To the residue was added 100 ml of10% hydrochloric acid, and the mixture was extracted with 100 ml ofethyl acetate. The ethyl acetate layer was successively washed 10%hydrochloric acid, saturated aqueous sodium hydrogen carbonate solutionand saturated saline solution, dried over anhydrous magnesium sulfate,and then concentrated under reduced pressure, which afforded 8.4 g ofcrude 4-benzyloxy-3-ethyl-5-methylphenyl benzoate (93% yield).

Then, 8.4 g of crude 4-benzyloxy-3-ethyl-5-methylphenyl benzoate wasdissolved in 100 ml of ethyl acetate, which was put into a reactionvessel, and the air in the vessel was replaced with nitrogen gas. Then,0.5 g of 10% palladium on carbon was added, and the nitrogen gas in thevessel was replaced with hydrogen gas, followed by vigorous stirring atroom temperature for 24 hours. The hydrogen gas in the vessel wasreplaced with nitrogen gas, after which the reaction mixture wasfiltered through cerite and the filtrate was concentrated under reducedpressure, which afforded 5.9 g of crude 3-ethyl-4-hydroxy-5-methylphenylbenzoate (95% yield).

To a mixture of 0.5 g of crude 3-ethyl-4-hydroxy-5-methylphenylbenzoate, 0.48 g of 3-(4-(trifluoromethyl)benzamido)propan-1-ol, 0.54 gof triphenylphosphine and 10 ml of tetrahydrofuran was added dropwise asolution of 0.41 g of diisopropylazodicarboxylate dissolved in 2 ml oftetrahydrofuran, while stirring at room temperature. After stirring atroom temperature for 24 hours, the reaction mixture was concentratedunder reduced pressure to give a residue. The residue was subjected tosilica gel chromatography, which afforded 0.87 g of3-ethyl-5-methyl-4-(3-(4-(trifluromethyl)benzamido)propyloxyphenylbenzoate (90% yield).

To a mixture of 0.87 g of3-ethyl-5-methyl-4-(3-(4-(trifluoromethyl)benzamido)propyloxyphenylbenzoate and 10 ml of methanol was added a mixture of 0.16 g of sodiumhydroxide and 2 m of water, while stirring at 0° C. After stirring atroom temperature for 24 hours, the reaction mixture was made weak acidicby the addition of 10% hydrochloric acid, and extracted with 50 ml ofethyl acetate. The ethyl acetate layer was washed with saturated salinesolution, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure to give a residue. The residue was subjected tosilica gel chromatography, which afforded 0.66 g of3-ethyl-5-methyl-4-(3-(4-(trifluoromethyl)benzamido)propyloxyphenol (94%yield).

The following are some specific examples of the intermediates of generalformula [IV] or [V] with their compound numbers and physical properties,if measured.

82) 3,5-Dichloro-4-(3-benzaomidopropyloxy)phenol

83) 3,5-Dichloro-4-(3-(4-chlorobenzamido)propyloxy)phenol

84) 3,5-Dichloro-4-(3-(4-trifluoromethylbenzamido)propyloxy)phenol

85) 3,5-Dichloro-4-(3-(4-trifluoromethoxybenzamido)propyloxy)phenol

86) 3,5-Dichloro-4-(4-benzamidobutyloxy)phenol

87) 3,5-Dichloro-4-(4-(4-chlorobenzamido)butyloxy)phenol

88) 3,5-Dichloro-4-(4-(4-trifluoromethylbenzamido)butyloxy)phenol

89) 3,5-Dichloro-4-(4-(4-trifluoromethoxybenzamido)butyloxy)phenol

90) 3,5-Dichloro-4-(3-(5-trifluoromethylpicolinamido)propyloxy)phenol

91) 3,5-Dichloro-4-(4-(5-trifluoromethylpicolinamido)butyloxy)phenol

92) 3,5-Dichloro-4-(3-(4-trifluoromethylbenzenesulfonamido)propyloxy)phenol

93)3,5-Dichloro-4-(4-(4-trifluoromethylbenzenesulfonamido)butyloxy)phenol

94)3,5-Dichloro-4-(3-(5-trifluoromethylpyridine-2-sulfonamido)propoxy)phenol

95)3,5-Dichloro-4-(4-(5-trifluoromethylpyridine-2-sulfonamido)butyloxy)phenol

96)3,5-Dichloro-4-(3-(N-(4-trifluoromethylphenyl)carbamoyl)propyloxy)phenol

97)3,5-Dichloro-4-(4-(N-(4-trifluoromethyiphenyl)carbamoyl)butyloxy)phenol

98)3,5-Dichloro-4-(3-(N-(5-trifluoromethyl-2-pyridyl)carbamoyl)propyloxy)phenol

99)3,5-Dichloro-4-(4-(N-(5-trifluoromethyl-2-pyridyl)carbamoyl)butyloxy)phenol

100) 3-Chloro-5-methyl-4-(3-benzamidopropyloxy)phenol

101) 3-Chloro-5-methyl-4-(3-(4-chlorobenzamido)propyloxy)phenol

102) 3-Chloro-5-methyl-4-(3-(4-trifluoromethylbenzamido)propyloxy)phenol

103)3-Chloro-5-methyl-4-(3-(4-trifluoromethoxybenzamido)propyloxy)phenol

104) 3-Chloro-5-methyl-4-(4-benzamidobutyloxy)phenol

105) 3-Chloro-5-methyl-4-(4-(4-chlorobenzamido)butyloxy)phenol

106) 3-Chloro-5-methyl-4-(4-(4-trifluoromethylbenzamido)butyloxy)phenol

107) 3-Chloro-5-methyl-4-(4-(4-trifluoromethoxybenzamido)butyloxy)phenol

108)3-Chloro-5-methyl-4-(3-(5-trifluoromethylpicolinamido)propyloxy)phenol

109) 3-Chloro-5-methyl-4-(4-(5-trifluoromethylpicolinamido)butyloxy)phenol

110)3-Chloro-5-methyl-4-(3-(4-trifluoromethylbenzenesulfonamido)propyloxy)phenol

111)3-Chloro-5-methyl-4-(4-(4-trifluoromethylbenzenesulfonamido)butyloxy)phenol

112)3-Chloro-5-methyl-4-(3-(5-trifluoromethylpyridine-2-sulfonamido)propyloxy)phenol

113)3-Chloro-5-methyl-4-(4-(5-trifluoromethylpyridine-2-sulfonamido)butyloxy)phenol

114)3-Chloro-5-methyl-4-(3-(N-(4-trifluoromethylphenyl)carbamoyl)propyloxy)phenol

115)3-Chloro-5-methyl-4-(4-(N-(4-trifluoromethylphenyl)carbamoyl)butyloxy)phenol

116)3-Chloro-5-methyl-4-(3-(N-(5-trifluoromethyl-2-pyridyl)carbamoyl)propyloxy)phenol

117)3-Chloro-5-methyl-4-(4-(N-(5-trifluoromethyl-2-pyridyl)carbamoyl)butyloxy)phenol

118) 3-Ethyl-5-methyl-4-(3-benzamidopropyloxy)phenol

119) 3-Ethyl-5-methyl-4-(3-(4-chlorobenzamido)propyloxy)phenol

120) 3-Ethyl-5-methyl-4-(3-(4-trifluoromethylbenzamido)propyloxy)phenol

121) 3-Ethyl-5-methyl-4-(3-(4-trifluoromethoxybenzamido)propyloxy)phenol

122) 3-Ethyl-5-methyl-4-(4-benzamidobutyloxy)phenol

123) 3-Ethyl-5-methyl-4-(4-(4-chlorobenzamido)butyloxy)phenol

124) 3-Ethyl-5-methyl-4-(4-(4-trifluoromethylbenzamido)butyloxy)phenol

125) 3-Ethyl-5-methyl-4-(4-(4-trifluoromethoxybenzamido)butyloxy)phenol

126)3-Ethyl-5-methyl-4-(3-(5-trifluoromethylpicolinamido)propyloxy)phenol

127)3-Ethyl-5-methyl-4-(4-(5-trifluoromethylpicolinamido)butyloxy)phenol

128) 3-Ethyl-5-methyl-4-(3-(4-trifluoromethylbenzenesulfonamido)propyloxy)phenol

129)3-Ethyl-5-methyl-4-(4-(4-trifluoromethylbenzenesulfonamido)butyloxy)phenol

130)3-Ethyl-5-methyl-4-(3-(5-trifluoromethylpyridine-2-sulfonamido)propyloxy)phenol

131)3-Ethyl-5-methyl-4-(4-(5-trifluoromethylpyridine-2-sulfonamido)butyloxy)phenol

132)3-Ethyl-5-methyl-4-(3-(N-(4-trifluoromethylphenyl)carbamoyl)propyloxy)phenol

133)3-Ethyl-5-methyl-4-(4-(N-(4-trifluoromethylphenyl)carbamoyl)butyloxy)phenol

134)3-Ethyl-5-methyl-4-(3-(N-(5-trifluoromethyl-2-pyridyl)carbamoyl)propyloxy)phenol

135)3-Ethyl-5-methyl-4-(4-(N-(5-trifluoromethyl-2-pyridyl)carbamoyl)propyloxy)phenol

136) 3,5-Dichloro-4-(3-(2-furancarboxamido)propyloxy)phenol

137) 3,5-Dichloro-4-(3-(2-furancarboxamido)butyloxy)phenol

138) 3,5-Dichloro-4-(3-(3-furancarboxamido)propyloxy)phenol

139) 3,5-Dichloro-4-(4-(3-furancarboxamido)butyloxy)phenol

140) 3,5-Dichloro-4-(3-(5-bromo-2-furancarboxamido)propyloxy)phenol

141) 3,5-Dichloro-4-(4-(5-bromo-2-furancarboxamido)butyloxy)phenol

142) 3,5-Dichloro-4-(3-(2-thiophenecarboxamido)propyloxy)phenol

143) 3,5-Dichloro-4-(4-(2-thiophenecarboxamido)butyloxy)phenol

144) 3,5-Dichloro-4-(3-(3-thiophenecarboxamido)propyloxy)phenol

145) 3,5-Dichloro-4-(4-(3-thiophenecarboxamido)butyloxy)phenol

146) 3,5-Dichloro-4-(3-(5-methyl-2-thiophenecarboxamido)butyloxy)phenol

147) 3,5-Dichloro-4-(4-(5-methyl-2-thiophenecarboxamido)butyloxy)phenol

148) 3,5-Dichloro-4-(3-(2-pyrazinecarboxamido)propyloxy)phenol

149) 3,5-Dichloro-4-(4-(2-pyrazinecarboxamido)butyloxy)phenol

150) 3,5-Dichloro-4-(3-(1-methyl-2-indolecarboxamido)propyloxy)phenol

151) 3,5-Dichloro-4-(4-(1-methyl-2-indolecarboxamido)butyloxy)phenol

152) 3,5-Dichloro-4-(3-(1-methyl-2-pyrrolecarboxamido)propyloxy)phenol

153) 3,5-Dichloro-4-(4-(1-methyl-2-indolecarboxamido)butyloxy)phenol

154) 3,5-Dichloro-4-(3-(2-quinolinecarboxamido)propyloxy)phenol

155) 3,5-Dichloro-4-(4-(2-quinolinecarboxamido)butyloxy)phenol

156) 3,5-Dichloro-4-(3-(5-methyl-2-pyrazinecarboxamido)propyloxy)phenol

157) 3,5-Dichloro-4-(4-(5-methyl-2-pyrazinecarboxamido)butyloxy)phenol

The following are formulation examples in which "parts" are by weightand the present compounds are designated by their compound numbers asdescribed above.

Formulation Example 1

Emulsifiable Concentrates

Ten parts of each of the present compounds (1) to (148) are dissolved in35 parts of xylene and 35 parts of N,N-dimethylformamide, to which 14parts of polyoxyethylene styrylphenyl ether and 6 parts of calciumdodecylbenzenesulfonate are added, and the mixture is well stirred togive a 10% emulsifiable concentrate of each compound.

Formulation Example 2

Wettable Powders

Twenty parts of each of the present compounds (1) to (148) are added toa mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium ligninsulfonate, 20 parts of synthetic hydrated silicon oxide fine powder and54 parts of diatomaceous earth, and the mixture is stirred with a mixerto give a 20% wettable powder of each compound.

Formulation Example 3

Granules

Five parts of each of the present compounds (1) to (148), 5 parts ofsynthetic hydrated silicon oxide fine powder, 5 parts of sodiumdodecylbenzenesulfonate, 30 parts of bentonite and 55 parts of clay aremixed, and the mixture is well stirred. Then, a suitable amount of wateris added to the mixture, which is further stirred, granulated with agranulator and then air-dried to give a 5% granule of each compound.

Formulation Example 4

Dusts

One part of each of the present compounds (1) to (148) is dissolved in asuitable amount of acetone, to which 5 parts of synthetic hydratedsilicon oxide fine powder, 0.3 part of PAP and 93.7 parts of clay areadded, and the mixture is stirred with a mixer. The removal of acetoneby evaporation gives a 1% dust of each compound.

Formulation Example 5

Flowables

Twenty parts of each of the present compounds (1) to (148) are mixedwith 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueoussolution containing 2 parts of polyvinyl alcohol, and the mixture ispulverized into fine particles having a particle size of not more than 3μm with a sand grinder, to which 40 parts of an aqueous solutioncontaining 0.05 part of xanthan gum and 0.1 part of aluminum magnesiumsilicate are added and then 10 parts of propylene glycol are added. Themixture is stirred to give a 20% water-based suspension of eachcompound.

Formulation Example 6

Oil Sprays

First, 0.1 part of each of the present compounds (1) to (148) isdissolved in 5 parts of xylene and 5 parts of trichloroethane. Then, thesolution was mixed with 89.9 parts of deodorized kerosine to give a 0.1%oil spray of each compound.

Formulation Example 7

Oil-based Aerosols

First, 0.1 part of each of the present compounds (1) to (148), 0.2 partof tetramethrin, 0.1 part of d-phenothrin, and 10 parts oftrichloroethane are dissolved in 59.6 parts of deodorized kerosine, andthe solution is put in an aerosol vessel. Then, the vessel is equippedwith a valve, through which 30 parts of a propellant (liquefiedpetroleum gas) are charged under increased pressure to give an oil-basedaerosol of each compound.

Formulation Example 8

Water-based Aerosols

An aerosol vessel is filled with 50 parts of pure water and a mixture of0.2 part of each of the present compounds (1) to (148), 0.2 part ofd-allethrin, 0.2 part of d-phenothrin, 5 parts of xylene, 3.4 parts ofdeodorized kerosine and 1 part of an emulsifier [ATMOS 300 (registeredtrade name by Atlas Chemical Co.)]. Then, the vessel is equipped with avalve, through which 40 parts of a propellant (liquefied petroleum gas)are charged under pressure to give a water-based aerosol of eachcompound.

Formulation Example 9

Mosquito-coils

First, 0.3 g of each of the present compounds (1) to (148) is mixed with0.3 g of d-allethrin, and the mixture is dissolved in 20 ml of acetone.The solution is uniformly mixed with 99.4 g of a carrier formosquito-coils (prepared by mixing Tabu powder, pyrethrum marc powderand wood flour in the ratio of 4:3:3) under stirring. The mixture iswell kneaded with 120 ml of water, molded and dried to give amosquito-coil of each compound.

Formulation Example 10

Electric Mosquito-mats

First, 0.4 g of each of the present compounds (1) to (148), 0.4 parts ofd-allethrin and 0.4 g of pipenyl butoxide are dissolved in acetone tohave a total volume of 10 ml. Then, 0.5 ml of the solution is uniformlyabsorbed in a substrate for electric mosquito-mats having a size of 2.5cm×1.5 cm×0.3 cm (prepared by forming a fibrillated mixture of cottonlinter and pulp into a sheet) to give an electric mosquito-mat of eachcompound.

Formulation Example 11

Heating Smoke Formulations

First, 100 mg of each of the present compounds (1) to (148) is dissolvedin a suitable amount of acetone. Then, the solution is absorbed in aporous ceramic plate having a size of 4.0 cm×4.0 cm×1.2 cm to give aheating smoke formulation of each compound.

Formulation Example 12

Poison Baits

First, 10 mg of each of the present compounds (1) to (148) is dissolvedin 0.5 ml of acetone, and the solution is uniformly mixed with 5 g ofsolid bait powder for animals (Breeding Solid Feed Powder CE-2, tradename by Japan Clea Co., Ltd.). Then, the removal of acetone by airdrying gives a 0.5% poison bait of each compound.

The following test examples demonstrate that the present compounds areuseful as active ingredients of insecticides. In these test examples,the present compounds are designated by their compound numbers asdescribed above and the compounds used for comparison are designated bytheir compound symbols as shown in Table 35.

                                      TABLE 35                                    __________________________________________________________________________    Compound                                                                            Chemical structure        Remarks                                       __________________________________________________________________________      (A)                                                                                                           Compound disclosed in JP-A 48-86835/1973                                    , page 23                                        - (B)                                                                                                        Compound disclosed in JP-A 49-1526/1974,                                     page 22                                      __________________________________________________________________________

Test Example 1

Insecticidal Test against Spodoptera litura

A 200-fold water dilution (500 ppm) of an emulsifiable concentrate ofthe test compound, which had been obtained according to FormulationExample 1, was absorbed at a volume of 2 ml in 13 g of an artificialdiet for Spodoptera litura, which had been prepared in a polyethylenecup having a diameter of 11 cm. Ten fourth-instar larvae of Spodopteralitura were set free in the cup. After 6 days, the survival of larvaewas examined to determine the mortality. The test was conducted induplicate.

As a result, it was found that the present compounds (1)-(7), (9),(11)-(21), (23)-(25), (27)-(30), (32)-(34), (44), (56), (58), (59),(67), (84), (86), (89)-(104), (108), (110), (111), (114)-(118), (120),(121), (124)-(127) and (129)-(133) exhibited the mortality of 80% ormore. In contrast, both compounds (A) and (B) for comparison exhibitedthe mortality of 0%.

Test Example 2

Insecticidal Test against Plutella xylostella

A water dilution (25 ppm) of an emulsifiable concentrate of the testcompound, which had been obtained according to Formulation Example 1,was sprayed at a sufficient volume over potted cabbages at the five leafstage. After air drying, ten third-instar larvae of Plutella xylostellawere set free on each pot. After 4 days, the mortality was determined.

As a result, it was found that the present compounds (1), (2), (4), (6),(7), (12)-(14), (18)-(21), (33), (34), (44), (58), (59), (67), (84),(86), (89), (90), (97), (98) and (108) exhibited the mortality of 80% ormore. In contrast, both compounds (A) and (B) for comparison exhibitedthe mortality of 0%.

Test Example 3

Insecticidal Test against Cnaphalocrocis medinalis

A water dilution (25 ppm) of an emulsifiable concentrate of the testcompound, which had been obtained according to Formulation Example 1,was sprayed at a sufficient volume over the foliage of cupped riceseedings (Nihonbare). After air drying of the chemical solution,third-instar larvae of Cnaphalocrocis medinalis were set free thereon.After 4 days, the mortality was determined.

As a result, it was found that the present compounds (1), (2), (4)-(7),(13); (14), (17), (18), (21), (32), (34), (56), (58), (59), (67), (89),(93) and (127) exhibited the mortality of 80% or more. In contrast, bothcompounds (A) and (B) for comparison exhibited the mortality of 0%.

Industrial Applicability

The present compounds have excellent insecticidal activity so that theyare satisfactorily effective for the control of noxious insects.

We claim:
 1. A dihalopropene compound of the general formula: ##STR171##wherein m is an integer of 0 to 4;n is an integer of 0 to 2; X's areindependently chlorine or bromine; Y is oxygen, NH or sulfur; and Z isoxygen, sulfur or NR₁₅ in which R₁₅ is hydrogen or C₁ -C₃ alkyl; R₂, R₃and R₄ are independently halogen, C₁ -C₃ haloalkyl or C₁ -C₃ alkyl; R₅,R₆ and R₇ are independently hydrogen, C₁ -C₃ alkyl or trifluoromethyl; Lis C═W, C(═W)NR₁₃, NR₁₃ C(═W), SO₂ NR₁₃, NR₁₃ SO₂, NR₁₃ C(═W₁)--W,WC(═W₁)NR₁₃ or NR₁₄ C(═W)NR₁₃ in which W and W₁ are independently oxygenor sulfur, and R₁₃ and R₁₄ are independently hydrogen, C₁ -C₁₀ alkyl, C₁-C₅ haloalkyl, C₂ -C₁₀ alkenyl, C₂ -C₆ haloalkenyl, C₃ -C₉ alkynyl or C₃-C₅ haloalkynyl; and R₁ is an optionally substituted thienyl or furyl.2. A dihalopropene compound according to claim 1, wherein R₁ is thienylor furyl optionally substituted with (R₁₆)_(s) in which R₁₆ is halogen,nitro, cyano, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₃haloalkoxy, C₁ -C₃ alkylthio, C₁ -C₃ haloalkylthio, C₁ -C₂alkylsulfinyl, C₁ -C₂ alkylsulfonyl, C₁ -C₂ haloalkylsulfinyl, C₁ -C₂haloalkylsulfonyl, C₂ -C₄ alkenyl, C₂ -C₄ haloalkenyl, C₂ -C₄ alkynyl,C₂ -C₄ haloalkynyl, amino, dimethylamino, acetamido, acetyl, haloacetyl,formyl, carboxyl, methoxycarbonyl, C₃ -C₆ cycloalkyl, (C₁ -C₂alkyl)aminocarbonyl, (di(C₁ -C₂ alkyl)amino)-carbonyl,phenyl optionallysubstituted with halogen C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxyor C₁ -C₃ haloalkoxy, benzyl optionally substituted with halogen, C₁ -C₄alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy, phenoxyoptionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁-C₄ alkoxy or C₁ -C₃ haloalkoxy, benzyloxy optionally substituted withhalogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃haloalkoxy, or pyridyloxy optionally substituted with halogen, C₁ -C₄alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy; and s is aninteger of 0 to
 4. 3. A dihalopropene compound according to claim 2,wherein the thienyl or furyl group is selected from the group consistingof 2-thienyl, 3-thienyl, 2-furyl, and 3-furyl.
 4. A dihalopropenecompound according to claim 2, wherein the thienyl or furyl group is2-thienyl, 3-thienyl, 2-furyl, 3-furyl, and L is C═W, C(═W)NR₁₃ or SO₂NR₁₃.
 5. A dihalopropene compound according to claim 2, wherein thethienyl or furyl group is 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, and Lis C(═W)NR₁₃ or SO₂ NR₁₃.
 6. A dihalopropene compound according to claim2, wherein the thienyl or furyl group is and L is C(═W)NR₁₃.
 7. Adihalopropene compound according to claim 1, wherein R₁₃ and R₁₄ areindependently hydrogen or C₁ -C₃ alkyl.
 8. A dihalopropene compoundaccording to claim 1, wherein L is C(═W)NR₁₃.
 9. A dihalopropenecompound according to claim 1 or 2, wherein R₂, R₃ and R₄ areindependently halogen or C₁ -C₃ alkyl.
 10. A dihalopropene compoundaccording to claim 1 or 2, wherein R₂ and R₃ are both chlorine, and R₄is hydrogen.
 11. A dihalopropene compound according to claim 1 or 2,wherein Y and Z are both oxygen.
 12. A dihalopropene compound accordingto claim 1 or 2, wherein R₅, R₆ and R₇ are independently hydrogen or C₁-C₃ alkyl.
 13. A dihalopropene compound according to claim 1 or 2,wherein R₅, R₆ and R₇ are all hydrogen.
 14. A dihalopropene compoundaccording to claim 1 or 2, wherein L is WC(═W₁)NR₁₃.
 15. A phenolcompound of the general formula: ##STR172## wherein R₂₀ is an optionallysubstituted thienyl or furyl; R₂ and R₃ are independently halogen, C₁-C₃ haloalkyl or C₁ -C₃ alkyl; R₅, R₆ and R₇ are independently hydrogen,C₁ -C₃ alkyl or trifluoromethyl; L₁ is C═W, C(═W)NR₁₃₁ or SO₂ NR₁₃₁ inwhich W is oxygen or sulfur, and R₁₃₁ is hydrogen or C₁ -C₃ alkyl; and mis an integer of 0 to
 4. 16. A phenol compound according to claim 15,wherein the thienyl or furyl group is 2-furyl, 3-furyl, 2-thienyl, or3-thienyl.
 17. a phenol compound according to claim 15, wherein thethienyl or furyl group is 2-furyl, 3-furyl, 2-thienyl, or 3-thienyl; andL₁ is C(═W)NR₁₃₁ or SO₂ NR₁₃₁.
 18. A phenol compound according to claim15, wherein the thienyl or furyl group is 2-furyl, 3-furyl, 2-thienyl,or 3-thienyl; R₂ R₃ are independently halogen or C₁ -C₃ alkyl; and L₁ isC(═W)NR₁₃₁ or SO₂ NR₁₃₁.
 19. A phenol compound according to claim 15,which is 3,5-Dichloro-4-(3-furancarboxamido)propyloxy)phenol.
 20. Aphenol compound according to claim 15, which is3,5-Dichloro-4-(4-furancarboxamido)propyloxy)phenol.
 21. A phenolcompound according to claim 15, which is3,5-Dichloro-4-(3-(3-furancarboxamido)propyloxy)phenol.
 22. A phenolcompound according to claim 15, which is3,5-Dichloro-4-(4-(3-furancarboxamido)butyloxy)phenol.
 23. A phenolcompound according to claim 15, which is3,5-Dichloro-4-(3-(5-bromo-2-furancarboxamido)propyloxy)phenol.
 24. Aphenol compound according to claim 15, which is3,5-Dichloro-4-(4-(5-bromo-2-furancarboxamido)butyloxy)phenol.
 25. Aphenol compound according to claim 15, which is3,5-Dichloro-4-(3-(2-thiophenecarboxamido)propyloxy)phenol.
 26. A phenolcompound according to claimed 15, which is3,5-Dichloro-4-(4-(2-thiophenecarboxamido)butyloxy)phenol.
 27. A phenolcompound according to claim 15, which is3,5-Dichloro-4-(3-(3-thiophenecarboxamido)propyloxy)phenol.
 28. A phenolcompound according to claim 15, which is3,5-Dichloro-4-(4-(3-thiophenecarboxamido)butyloxy)phenol.
 29. A phenolcompound according to claim 15, which is3,5-Dichloro-4-(3-(5-methyl-2-thiophenecarboxamido)propyloxy)phenol. 30.A phenol compound according to claim 15, which is3,5-Dichloro-4-(4-(5-methyl-2-thiophenecarboxamido)butyloxy)phenol.